


Little Cow at Poughkeepsie High

by still_ill



Category: Supernatural
Genre: ...but a loving creep Dean, Age Difference, Alternate Universe - High School, Bottom Castiel, Calf!Cas, Coaxing, Come Eating, Cow!Cas, Cow/Human Hybrids, Cowboys & Cowgirls, Creep Dean, Dom/sub Undertones, Embarassment, Human Dean, Humilation, Hybrids, Lactation Kink, M/M, Male Lactation, Nipple Play, Praise Kink, Shy Castiel, Slight reluctance kink, Student Castiel, Supernatural Kink Meme, Teacher Dean, Top Dean, Underage Sex, but definitely not a western, dubcon, think catboys but with less meow and more moo
Language: English
Status: In-Progress
Published: 2016-06-13
Updated: 2016-07-09
Packaged: 2018-07-14 20:08:44
Rating: Explicit
Warnings: Underage
Chapters: 5
Words: 21,278
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7188269
Author URL: https://archiveofourown.org/users/still_ill/pseuds/still_ill
Summary: <blockquote class="userstuff">
              <p>From the spn-kinkmeme prompt from days of yore:<br/>For whatever reason a teen Castiel had little A cup tits that need to be milked. It’s humiliating for him but Dean is very coaxing with him, milking Castiel’s nipples and sometimes drinks right from them.<br/>I’d love a scene with Dean fucking Castiel while sucking his milk down.<br/>Bonus if it’s extremely taboo for Castiel to let Dean suckle him during sex but the boy really gets off on it.<br/>A million bonuses if Castiel is some sort of sub-human cow/human hybrid.<br/>Prefer Dean to be older(25-30) and Castiel young,(14-17)</p><p>--<br/>“You weren’t what, baby cow?” he said, fingers gently circling around Castiel’s areolas.<br/>“Oh, Dean, Dean, please, this is too much. I, I can’t, I need-" and then Castiel let out a long, low moan as Dean finally began working his right nipple. A little stream of milk dribbled out.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I seriously always loved this prompt and was always sad it never got finished over at LJ. I almost didn't write in the cow/human hybrid part for reasons beyond having to work around not using the word cowboy, but I'm very, very glad I did. Little calf!cas sounds fucking adorable if I do say so myself. 
> 
> Cas is 15, Dean unspecified but at least ten years older. Pay attention to the tags, please. Dean is not on his best behavior in this fic.

**Notes for the Chapter:**

> Uhm, the amazing [SupernaturalMystery306](http://archiveofourown.org/users/SupernaturalMystery306/profile) blessed me with this AMAZING banner. You should all go to her [tumblr](http://fancythingsandgossamerwings.tumblr.com) and thank her for her beautiful art!!

                                                     

 

 

There were plenty of human-animal hybrids at Poughkeepsie High: Cats, Dogs, Rabbits, even a few lambs. What there weren’t a lot of were calves. Most of their kind kept to homeschooling or Cow only communities. However, a movement towards desegregation was gaining ground, which is how Castiel Novak, a fifteen year old calfboy, found himself at a public, mixed school for the first time in his life. His parents, realizing the world was changing, had thought it best for the boy to be on the right side of progress and give him a head start over the other little cows.

Castiel was small for his age, had naturally tan skin, dark, wavy hair and the biggest, bluest eyes Dean Winchester had ever seen. He had baby calf ears and a cute, little tail that matched the color of his hair and looked velvety smooth. He had a round ass and beautiful, plush lips, but what Dean appreciated most were his A cup tits. The first day Castiel had showed up in class, perky breasts subtly bouncing up and down as he walked to his desk, Dean had to sit down lest the children catch a glimpse of how much he was enjoying the view. And whenever he got close to the boy there was a sweet, milky smell that Dean never wanted to live without. He hadn’t ever had a calf in one of his classes. He was now finding this a terrible tragedy.

Castiel hadn’t worn a bra the first few weeks of school, it was painfully obvious. His little titties would jiggle with the slightest movement. And Dean had purposefully turn the room temperature down so he could sneak glances of Castiel’s nipples pebbled against his shirt. One day the boy had even worn white. Dean could just barely make out his darkened areolas pressing up against his shirt. As soon as Dean got home he nearly stripped his dick thinking about the little cow.

After the third time Dean jerked off to his new student he admitted to himself that he might have a bit of a crush. He had a hard time thinking about anything besides Cas. He had even lost interest in the little fox Bella that he’d been messing around with for the past few months.

All of his porn searches had slowly switched from a wide variety to just Cows, which had a lot less content due to their standoffishness. But what it lacked in quantity it made up for in quality. Video after video showed the human hybrids being fucked in all kinds of ways, but seldom did they have what Dean really wanted to see: milking.

There were plenty of non-sexual milking videos. Dean indulged in them at first, watching cows get their aching udders squeezed for morning coffee or cake batter. There was even a good deal of nursing videos – which Dean liked the best. Cows letting different people, sometimes two at a time, suck at their tits until there was nothing left. It left their nipples red and swollen and they were obviously aroused, but they never touched.

Dean thought all these videos were fine, but he wanted more, he needed more. He considered himself a simple man with simple tastes, and this simple man with simple tastes wanted to watch little cows getting fucked and nursed at the same time.  He couldn’t understand why it was so forbidden in Cow culture. Nursing was okay, fucking was okay, so why not have the best of both worlds?

When Dean found an online community of people who felt the same way, it warmed his heart. There he found lots of art, stories, and, best of all, a few video links to his new found fetish.

He’d watched almost all of them within a week, and then started re-watching his favorites over and over again. The videos had all sorts of calves: fat, thin, light, dark, and he loved them all. And yet every time he came he was picture one calf in particular, with sweet, blue eyes and pretty pink lips. The day he’d found a video of a dark haired calf sucking off a huge cock while a pudgy, blonde bunny suckled his udders Dean thought he’d died and gone to heaven.

Much to Dean’s dismay, the calfboy Dean was jonesing after had started wearing bras. He could still get the boy’s nipples to poke through his shirt if he turned the temperature down far enough, but then he risked the boy putting on the hoodie he had started bringing to class. And he sincerely missed how his cute, little udders would jiggle or bounce. Once, before Cas had started wearing bras, Dean had been able to graze a hand over a tit and play it off as an accident. Castiel’s ears and tail had twitched, and he'd jumped back. Dean had affected a totally clueless air and asked Castiel if anything was wrong, if he had seen a bug or something. Cas just quietly shook his head and looked down, but Dean still caught the pink flush in his cheeks.

With all this weighing on Dean’s mind everyday it was amazing that he hadn’t tried to make a move on the boy yet. True, he was still a little young, but he had hit sexual maturity and within must hybrid cultures, including Cow, it meant they were old enough to engage in sexual acts. It also, though maybe it should have, didn’t bother Dean that he was Cas’ teacher. The boy was smart, smarter than him probably, so it wasn't like he'd be influencing Dean to give him better grades.

About a month into school Dean noticed Castiel had started rubbing at his tits when he thought no one was looking. It would be very casual, everybody’s head bent down doing their work when Dean would see, out of the corner of his eyes, Castiel quickly bringing a palm up to an udder and giving it a quick rub. Or sometimes Cas would be leaning forward in his desk, and Dean would notice that he was pressing his tits up against the edge of the table and then slightly rock back and forth. He couldn’t believe his luck and tried not to stare too much and scare Cas away from satisfying whatever urges he was feeling. Castiel’s face always looked relieved after he had applied some pressure to his breasts. Dean longed to help the boy.

A few times he had caught the calf staring at him. Dean had been brave enough to wink once. Castiel’s eyes got huge, and he hadn’t looked back up at Dean for the rest of class. It made Dean a little nervous for the next few days, halfway expecting someone from administration to reprimand him for flirting with students during class, but nothing ever happened. It gave him hope. Maybe Castiel wanted him too but was still just too shy. He was probably pretty sheltered, Dean reasoned.

One night, bored and rereading one of the nursing stories he had kind of written off before, Castiel’s rubbing behavior was explained. Lactation. Dean immediately started researching Cow hybrid lactation and found out some illuminating facts. At some point, a year or two after puberty, Cows began to produce milk which they would continue making for the next three to four decades. And, often enough, a young Cow would have trouble expressing the milk and would need to learn the proper techniques for milking. Some calves had even more stubborn tits, and needed lots of messaging and coaxing before they could release. If they weren’t milked often enough it could become quiet painful. In addition, sometimes the nubs would become overly sensitive or itchy.

Dean thought Castiel must be awfully miserable and wondered if he had begun milking himself, or if the little cow even knew what was going on. He wondered if somebody at home helped him, and what they did with the milk after. Did they use it for breakfast, store it up for later, throw it away?

Dean immediately began watching YouTube videos on proper milking techniques. His dick had already started fattening up while reading, but now it was hurting and straining against his slacks. Not wanting to get his work pants soiled he hurriedly pushed them off, briefs going down as well. Dean ran his thumb over the slit, pressing down until he gasped, and then brought the pre-come down his shaft. He did this a few times before he started to vigorously jerk off. He let out a tiny whimper as he thought about his little cow licking up all his jizz, rubbing it all over his tits, and then letting Dean lick and suck on his udders, combining Cas’ sweet cream with his own bitter come.

He moaned as he imagined Castiel’s lips around his cock while his little udders dangled in his face. Dean felt his balls tightening, getting ready to release. With one hand cupping his sack and the other twisting up and down his throbbing cock, Dean shot hot, thick ropes of come all over his stomach and legs. After coming down from his blissful high, he looked down at his mess and sighed, desperately wishing his little cow would come and clean him up.


	2. Chapter 2

**Notes for the Chapter:**

> Safe to say this chapter got away from me...
> 
> Gonna be a bit longer before I update this one again. I owe my first fic a time stamp.

Late one day after school, Dean saw Castiel crying in the hallway, hands rubbing at his chest and face contorted in frustration. Dean had been on his way home but quickly stopped. He would have stopped for any student, but this… this was quite possibly the miracle he’d been praying for. Dean approached the calfboy slowly, letting out a, “Hey, Cas,” when he got closer.

Castiel looked up at him, precious face looking pathetically tear-strung, ears plastered down. He let out a groaned, “No, no, no,” before hiding his face in his palms against his locker, arms still pressed against his chest.

“Hey, buddy,” Dean coaxed. “What’s wrong?”

Castiel just stayed silent and shook his head.

Tentatively Dean stretched out a hand and placed it on the boy’s shoulder. He heard Castiel take a big, shuddering breath but kept his face hidden.

“Hey, it’s okay. You can cry, guys cry all the time. It’s no big deal. You don’t need to be embarrassed, ba- buddy.” He waited for a moment before continuing, “Hey, Cas. Talk to me.”

Castiel hiccupped and then whispered something inaudibly.

“What’s that?” Dean asked, voice as calm as he could make it.

“Hurts,” Castiel said, slightly turning his head but still not looking up at Dean. His face was red, tears still being blinked form his eyes.

Dean’s heart clenched. Of course this was the opportunity he’d been praying for, but he hadn’t factored in actual emotions. The kid was hurting, and Dean wanted to fix it.

Castiel turned enough so that he was almost facing Dean, which the man took as a good sign.  
He was glad to see that though Castiel was wearing his hoodie, it was unzipped, and Dean could make out the shape of his perky udders. It looked as if they were getting too big for his bra. Maybe he was just that loaded with milk.

“What hurts, Cas?”

The calf looked down at his tits and then covered his face again.

“Hey, hey,” Dean pacified, putting his hands on both of the little cow’s shoulders. “It’s okay. They’re hurting because you’re growing up, right? Turning into a big Cow?”

Castiel lowered his hands, still not looking directly at Dean, and shrugged his shoulders.

Dean debated on what to say next and decided to just go for it. Pussyfooting around had never been a strong point.

“Why don’t you come into my room, and we can talk about it? Or at least clean you up a bit?” he said with a smile, eyes crinkling at the corners.

Castiel looked briefly confused, probably not sure what talking would do, but shook his head, finally looking at Dean and giving him a small smile.

“Atta boy!” Dean said while clapping him on the back. Castiel wiped his face with his sleeve, and if he noticed that Dean’s hand didn’t just stay on his shoulder but migrated to the middle of his back, he didn’t say anything.

Once they were in the classroom and the door shut, Dean sat down on his desk motioning for Castiel to stand in front of him. He had grabbed a few tissues and started cleaning up the rest of the calf’s face. Castiel remained impassive, but his little ears fluttered as Dean gently wiped away the tears.

“There you go. Lookin’ better already!” he said with a grin.

Castiel rolled his eyes but returned Dean’s smile anyways.

“Thanks,” he said, his voice still sounding distraught.

“Hurts pretty bad then?” Dean asked.

Castiel nodded.

“Is that pretty normal?”

Castiel shrugged.

“Look, Cas, I don’t know too much about Cows, but I’m pretty sure there’s a way to help ease the pain. Haven’t your parents talked to you about…” and he just trailed off, motioning back and forth at the calf’s chest.

“Not really,” Cas said. “They just told me I’d have to start getting milked soon and left me with a pamphlet on the joys of producing. It didn’t really give any instructions though, just…” and he stopped himself, clearly embarrassed.

Dean, for his part, kept his face neutral.

“Just what, Cas? It’s okay, you can tell me. You can talk to me about whatever. I’m not gonna think it’s weird - or nark on ya,” he said with a wink.

Castiel scoffed in amusement.

“Just nothing, Mr. Winchester. My chest hurts, I didn’t know why, I asked my parents, they were useless, I tried to help myself, I was useless, everything sucks and I just, it aches, Mr. Winchester. It aches so much. I… I think I’m broken.” Cas said, chin quivering, eyes filling back up with tears.

“Hey, hey, Castiel, none of that. You’re not broken. You hear me? You are not broken. I mean, if you need help…” Dean trailed off, biting his lip.

Castiel sharply inhaled and shook his head.

“I… I don’t think so, Mr. Winchester. It’s uh. I’m sure you just didn’t know, but that’s uhm, something just for family and uhm…”

“Ahh,” Dean said, feigning realization. “Okay, I gotcha.” Dean rubbed his hands on his thighs. “Well, in any case, you can cut the Mr. Winchester crap and call me Dean outside of school hours. Hate sounding like such an old man.”

“But you’re not old, Mr. Winchester!” Cas said, eyes wide and ears pointed forward.

“Ha, kind of you,” he said, trailing a finger slowly, deliberately, up and down his thigh. He noticed Castiel’s hands twitch, one moving to touch his thigh too. He probably didn’t even realize he was mimicking Dean.

“Also, what did I just say about Mr. Winchester?”

“Sorry, Mr… Dean,” Castiel blushed furiously. “It just… I mean I guess it’s force of habit.”

Dean nodded in an understanding manner.

“Okay,” Dean said, slapping his hands on his thighs, making Cas jump. “What are we gonna do about your situation?”

Castiel blinked and looked back down at his chest.

“I dunno,” Cas replied, averting Dean’s stare.

“Hey, Cas, look at me.” Big blue eyes met his own green ones. “You have a problem, kiddo, and instead of hiding from it, and ignoring it, and hoping it goes away, and then it getting so bad that you end up crying in a hallway, you need to face it head on. If you don’t trust me to help, that’s fine, but you need to do something. I dunno, maybe we could look up some information, or some videos? Maybe you’re not doing something quite right?”

“It’s not that, that I don’t trust you, M – Dean. It’s just…”

“Hey, Cas, I get it. You don’t have to explain anything to me. But I want you to know that you _can_ trust me. That I’m an adult. I’m your teacher, and I would never do anything to hurt you.”

“I know that, Dean, I just…”

“Just what?”  Dean asked, eyebrow raised with a gentle smile.

“It’s _embarrassing_ ,” replied Cas. “It’s so embarrassing. None of the other boy hybrids here have chests like mine, not even the _catboys,_ and it’s nice of you to offer, really, but I should do it on my own. I…I should get going, Mr. Winchester. My parents will start to worry about me if I’m gone much longer. Thanks anyways.”

“Hey, not so fast, Cas! I mean… honestly, it seems like your parents don’t care much, Castiel, but I’ll take you for your word that they do. Look,” Dean said, swiping his hand through his hair. “You’re obviously in a lot of pain, and if you don’t trust me that’s one thing, but if it’s pride that’s stopping you from getting help, well, that’s not very brave to me.”

“It’s not, not… I’m not saying you’re not trustworthy, Mr. Winchester.”

Dean held up his hands. “Okay, okay, so it’s pride then? Well, Cas, listen to me, buddy. Who cares if you’ve got A cups, ya know? It’s normal for little cows like you to have them, so who cares if none of the other boybrids do? And, honestly, Cas, it’s not like I’ve been _trying_ to look, but they’re obviously swollen, your spilling over that tight, little cup of yours. And if you think I’m asking to help just so I can laugh about the little cow with swollen baby tits then you don’t know me at all, Cas. Not at all.” Dean breathed in deeply, trying to get in as much as Castiel’s sweet smell in case he had just blown his chance.

Castiel’s chin started quivering again, but instead of running out the door he slowly let his backpack drop to the floor and removed his hoodie as well, throwing it on a nearby desk. Dean didn’t say anything, he just watched Castiel, wanting to let the boy feel like he had all the control.

Castiel’s hands went to the edges of his shirt, and Dean’s breath hitched, his stomach suddenly tied up in a knot. Castiel hesitated, took a deep breath, and then lifted his shirt off, placing it on the ground.

His arms immediately crossed over his little tits, trying to hide them even though that defeated the purpose. He was wearing a plain white bra, nothing fancy, but it had a tiny little bow in the middle. Dean nearly melted, and had to rearrange his legs on the desk. His dick was starting to stiffen. He knew he wouldn’t be able to hide his erection, but hopefully Castiel would be too preoccupied to notice. Unless Castiel wanted to notice…

“Okay, buddy,” Dean said, licking his lips. You can leave your bra on, I guess, if that makes you feel better. You could maybe… pull your breasts out of the cups or… maybe keep ‘em in and get your bra soaked. Even a milk soaked bra is gonna feel better than how you feel now, I promise.”

Castiel bit his bottom lip and kept his eyes glued to the floor. “I… I don’t know, Mr. Winchester. I, ugh, I don’t think I should be doing this after all. My mom… She, I mean Cows in general they don’t… This is-“ Castiel took a deep, shuddering breath.

Dean leaned forward and started to sooth, “Hey, Cas, it’s okay, buddy. It’s okay. We’re not doing anything wrong. We’re just trying to make you feel better, okay? Nothing wrong with getting a little help to feel better, right? Tell you what, you let me help you get some relief and I’ll tell you something about me, anything you wanna know. You can make it as embarrassing as you’d like. First time I popped a boner? No problem. First time I tried to take a bra off? Sure. It was a ridiculous fail, by the way.”

Castiel gave a small laugh and looked up at Dean.

“You’re not gonna tell anyone, are you, Mr. Winchester?”

“No way, Cas. It can be our little secret, okay?”

Castiel nodded his assent and looked back down. Slowly he lowered his hands, and Dean could once again bask in the baby titties displayed so openly before him. Unconsciously he licked his lips and looked up to see Cas doing the same.

“Okay, Cas, how do you want to do this? Personally I think it should be hands actually on, but I get it if you’re too scared, or if that’s too weird or something.”

“’M not scared” Castiel said, face frowning.

“Are you sure, buddy? It’s okay to be scared. It’s your first time to have somebody do this after all.”

“I’m _not_ scared!” Castiel reaffirmed, stomping a leg. Dean loved the way his little udders jiggled, his right tit was so close to falling out of its cup.

“Alright, alright!” He said with a smile.

Then he brought his hands up to Castiel’s shoulders and started rubbing them up and down slowly. Castiel’s ears and tail twitched but eventually his body started to relax under Dean’s hands. Dean squeezed his arms and then, slowly, watching Castiel’s face, brought them over Castiel’s tits. He didn’t squeeze, he just let them rest there before running his fingers down the boy’s chest, very lightly.

“Mr. Winchester,” Castiel gasped, making Dean’s dick twitch.

“Dean,” he corrected.

“Dean, I- I don’t-“

“Shh, little cow, shh. Stop worrying about it and let me help you. It’s okay, I promise. It’s okay.” Dean said, voice barely above a whisper.

Castiel nodded, blushing like mad. Even his chest started turning a beautiful shade of pink.

“Good little cow, very good. Okay, now I’m going to put my hands back on your udders, okay? It’s okay if I call them udders, right, Cas? That’s what they are, after all.”

Cas just stared back at him, voice caught in his throat, but managed a tiny nod.

Dean continued, “That’s right, Cas. Little calf. You’ll be a big Cow soon, and big Cows know how to take care of their problems, right? And right now your udders are so swollen, little one. They’re filled with milk, and they hurt, and you can’t get the milk out ‘cuz you’re still just a little baby cow. But I’m gonna help you, alright? I’m gonna milk you, and you’re gonna feel so much better, Cas.”

Castiel just kept staring at Dean, as if he were caught between being enraptured and terrified.

Dean swallowed and placed his hands back on Cas’ small mounds. He was getting so hard.

 “Tell me to stop, and I’ll stop, Cas,” he breathed, one more time.

Castiel didn’t say anything, just continued staring at Dean and softly panting. His ears, Dean realized, were much more expressive. They had been lying down, but now they had perked up and kept twitching.

“Okay, buddy. I’m gonna look at them, just take a peak. I need to see if there’s anything wrong, okay?” Dean had no idea what he was talking about, but Cas seemed to buy it.

“Just.. don’t laugh. _Please_.”

Dean frowned. “Are other people laughing at you, Cas?”

Castiel’s lips formed a hard line. “S-some of the older boys like to laugh at me in the locker room.”

“Cas,” Dean responded frankly, “those boys are fucking idiots.”

Castiel smiled again.

“That’s right, big guy. They don’t matter. Now let’s see what we can do about this pesky little problem you’ve got.”

Castiel’s hands fluttered, as if he wanted to cover himself again, but he didn’t stop Dean as the older man’s fingers squeezed down into the soft flesh. He ran a finger over the edge of the cup, loving the way Cas’ silky skin felt next to the fabric. He pressed down on the bow between the two mounds, then brought his palms back over the udders, cupping them lovingly.

“Bet your back hurts some days too, huh?” Dean said, lifting the tits up slightly, trying to test their weight.

Castiel nodded his head and replied, “How did you know?”

“Small little body like yours is bound to feel a strain from these udders, even if they’re still little baby ones. They don’t look so small now though, Cas. Geeze, there sure is alotta milk in these guys, huh? How long have you been hurting like this?”

Dean, of course, knew the answer already.

“About… a week and a half?” Castiel replied.

More like three, Dean thought.

“Wow, a week and a half? That’s so long, Cas! It’s a good thing you came to me with this problem, buddy, or else your itty bitties might have exploded! Now, just relax. I’m gonna pull your cups down and inspect your udders, okay, little cow?”

“O-okay, Mr. Winchester. Dean.”

“Good boy.”

Dean didn’t miss the way Cas’ ears fluttered at the praise.

Dean lowered the left cup first, then slowly lowered the right one, the one that was obviously bigger. Castiel’s nipples were hardening up fast. They were a beautiful, dusky brown color. The nipples were a big larger than non-Cows, but Dean thought they looked perfect on him.

“Oh, Cas,” Dean whispered, unable to help himself. He tried to reel himself in, but it was taking every ounce of his strength not to snatch the calfboy up and latch on to a tit and start sucking. The sweet smell from Cas had seemed to amplify, going straight to his dick which was now fighting the confines of his pants. Dean made eye contact with Cas and palmed himself, hoping the little cow wouldn’t notice.

Dean reached out and lifted a freed a tit a bit more from its cup, listening to Castiel try to hide his gasp. The boy was so responsive, already so much better than Dean had imagined and he had just begun.

Dean put his palms back on the udders and started slowly moving his fingers across. He then poked one, just above the areola, and watched it jiggle, plump with milk. He was staring at Castiel’s tits the entire time, enjoying the way his flush had gotten as far as the breastbone between his two mounds, until the calfboy interrupted his thoughts.

“Mm-maybe this wasn’t such a good idea, Mr. Winchester,” came his small voice.

“Aw, Cas, baby, if you feel that way then okay. But we’re already here. Don’t you think it’d be smarter just to finish? Did I do something bad? Am I hurting you?”

“N-no, Mr. Winchester. You- you’re not hurting me.” Castiel said, fingers fidgeting with the tops of his pockets.

“I’m not hurting you, little cow? Well, then are we doing something bad? How could it be bad, if it’s not hurting you, and if it’s going to fix you? Cas, I’m only trying to help. I’m staying late at work just for you. Which I don’t mind, sweetheart. I’m happy to help if I can.”

“It’s just that, this is… please, this is – I shouldn’t be doing this. I- I’m of age. I shouldn’t need somebody to do this!” Hey was blushing bright red, fists balled up.

Dean knew this was embarrassing for the kid. Then a brilliant idea struck.

“Hey, Cas, Cas, it’s okay. If this is too hard for you we’ll quit. We can wiki some info and get you out of here. But why don’t you try turning around first. Maybe it’ll be easier if you don’t have to look at me?”

“O-okay,” he stammered, nodding his head. Dean relinquished his hold and let the calfboy turn around. Then he slid off the desk and slipped up behind Cas. He had given himself the perfect vantage point to watch his own hands work Castiel. The went under the boys arms and rested on his ribs.

“Better?”  he asked.

Castiel gave a slight nod. Dean’s hands slid up, over the pushed down bra and cupped his small tits again, loving how taut they felt, how well they fit in his palm.

“That’s good, little cow. That’s good. I’m gonna start now, if that’s okay with you. I’m going to slowly start messaging your udders and then start working them for milk, okay?”

Castiel’s ears twitched furiously while he nodded. His cute, little tail wished rapidly from side to side, and Dean could see the back of his neck turning red and goosebumps spread across his arms.

“Can I start massaging your udders, little cow? Is that okay, baby?”

Castiel whispered his consent, and Dean finally started working his fingers into the tits, not even noticing his second slip up with the pet name. Castiel immediately arched his back and gasped. The pressure probably felt amazing for him. His little tail stopped swishing and shot out straight, going between Dean’s legs.

“Good little cow, good. I’ve got you, Cas. Don’t worry, okay? I’ve got ya.”

Castiel whimpered and shifted the weight on his feet. Dean’s palms kept on rubbing against his nipples as he kneaded the calf’s flesh. He felt them growing even harder, the areolas puckering under his ministrations. He longed to pull on the tits, suck them into his mouth, drink from the source, grind his throbbing erection into the boy’s pert ass. Instead he kept on messaging the boy’s breasts until he saw Castiel’s shoulders lose some of their tension.

“That’s it, sweet, little cow. Bet it feels pretty good, huh? My big hands on these little udders. I’ve seen you in class, you know. When you didn’t think anybody was looking, rubbing on them, squishing them against the desk. You don’t have anything to be embarrassed about it though, baby cow. It’s all normal.”

“Dean,” Castiel whined, pushing his chest harder into Dean’s hands.

“Did you know I saw, baby? Were you putting on a show for me? It’s okay if you were, ya know. Cute little cow like you should do what he wants.”

“I-I wasn’t-” Castiel’s interrupted himself with a gasp because Dean had just squeezed his tits with vigor.

Dean leaned in closer to the calfboy’s ear but still making sure not to touch Cas with this hard on.

“You weren’t what, baby cow?” he said, fingers gently circling around Castiel’s areolas.

“Oh, Dean, Dean, please, this is too much. I, I can’t, I need-“ and then Castiel let out a long, low moan as Dean finally began working his right nipple. A little stream of milk dribbled out.

It was a happy accident, Dean knew that focusing on the nipples wasn’t actually how he’d need to milk Castiel, but seeing it had caused his self restraint to snap.

“You wanna spill your milk onto this cute little bra, or should I grab a cup, Cas?”

“C-cup, Mr. Winch-Ah!” Castiel yelped because Dean had just pinched an elongated nipple, “-Dean. Please, a cup, Dean. Don’t make me go home like that, please M- Dean, please don’t.”

“Okay, baby. Okay, don’t have to do anything you don’t wanna do, right?”

Quickly Dean reached back and grabbed his empty travel mug, screwed off the lid, and shoved it into Castiel’s hands. He glanced down and quickly admired the dimples next to the beginning of Cas’s tail and beautiful ass before closing the distance and bringing both hands back to those beloved udders.

“So swollen, baby. They’re so swollen and sore. Gonna make you feel so much better, you know. Gonna give you what you need. Cute, little cow like you shouldn’t be walking around in pain, too ashamed to come to his teacher and get those sweet little titties milked. Be a good boy and always come to your teacher when you need help, okay, little cow? Don’t be shy, this is for your own good!”

Castiel whimpered and Dean positioned fingers from both hands about an inch away from Castiel’s gorgeous nipple and waited for the boy to position the cup. He had picked the right one, the fullest one, hoping the Castiel appreciated the gesture. With trembling hands Cas brought the mug up to his tit and with that Dean pushed his fingers back toward’s Cas’ chest and then rolled them forward. A beautiful, solid stream of milk shot out, hitting the back of the cup with an audible ping.

Castiel could apparently no longer hold back, and the boy threw his head back and groaned with sweet release. A soft ear tickled Dean’s cheek, but he paid it no mind as he repeated his previous action. Castiel’s groans alternated with whimpering as Dean coaxed the stubborn liquid out of its home. The first streams had come out easily, but every now and then it would slow down. Dean could feel that there was still more that needed to be released, so he diligently kept milking.

“Stubborn little titty, wouldn’t you say, Cas? Being so naughty, so full but not wanting to let it out. Don’t worry, baby, I’m gonna get every last drop.”

Castiel’s hands balled up into fists, and he bit down on his lower lip.

Dean’s dick was so hard it hurt, but he kept repeating to himself that Cows didn’t mix milking with sex, and if he ever wanted a shot at getting Cas to do both he’d need to play it cool for right now. Well, as cool as possible. He told himself to lay off all the blabbering and calling Cas baby, but he’d never had good control over his mouth.

The last bit of milk shot out of the first tit, and Dean couldn’t help running his fingers through the warm liquid that had dribbled all over Castiel’s boob. He swirled the pads of his fingers around in it and then brought them up over the nipple, lightly plucking at it. It had grown a beautiful shade of reddish brown, and Dean could still see the red from where his fingers had been kneading the flesh around it. On impulse he gave the nipple a little shake, as if it were a tiny dick and he was clearing it of any residual urine, and then he took a deep, calming breath.

“Okay, Cas, gonna switch to the second one. You doin’ okay, buddy?”

Castiel barely shook his head, fists still balled up and chest still a delicate pink. His ears were laying flat on his head again and his tail was drooping between his own legs. The poor kid had gotten embarrassed all over again.

“Hey, Cas, it’s okay, remember? This is all perfectly natural. You were made to be milked, right? That’s why you’ve got these lovely little udders perched on your chest. There’s nothing wrong with them, and there’s nothing wrong with what we’re doing, right? Just a teacher trying to help out a good student. A kid who deserves to not feel bad, alright?”

Dean brought his hands up to the juncture between Castiel’s shoulders and neck and started massaging, trying to loosen the kid back up. Cows expressed milk better when they were relaxed. Incidentally, he realized he was rubbing Cas’ milk into his own beautiful skin. He was so soft and warm, smelled so sweet. Dean felt a fat glob of precome leak out of his dick. He was no longer certain that he wouldn’t come in his pants behind Cas.

Castiel’s hands slowly unclenched, and he nodded.

“Want me to get started on the second one, Cas?”

Cas just barely nodded his head.

“Gotta hear you say yes, Cas.”

Dean’s hands went around his little body again, fingers resting over the bra cups that had been pushed down. He noticed the right one was now pretty damp. He closed his eyes and counted to ten.

“I-I’m ready, Mr… Dean.”

Dean heard him swallow. His mouth had probably gone dry.

“You thirsty, ba-buddy?”

Castiel shook his head, and Dean silently cursed. He’d have to get Cas to drink his own milk some other time.

“Okay, well, in that case you tell me what you’re ready for, and we’ll get to it!”

“W- ready for? What do you mean?” Castiel’s ears swiveled back, as if they were trying to look at Dean.

“You gotta tell me, Cas. Use that big ole brain of yours and tell me in a complete sentence what you want me to do.”

Castiel’s breath hitched. He swallowed again and then in a quiet voice told Dean, “I’m ready for you to… milk me, sir.”

“Ah, Cas,” Dean sighed, daring to draw this out even longer. “Milk what?”

“I’m… I’m ready for you to milk my udder, Dean.”

“Perfect. You’re so perfect.”

Castiel bit back a smile and Dean started working his left tit, not bothering to wait for him to hold the cup up. Castiel jerked it forward and spashed some of the milk out onto his stomach. Dean stifled his groan as best he could but assumed Castiel heard him anyway. The boy’s eyes shut and he pressed his lips together, but he didn’t make any move to get away. In fact his tail had sprung back up again, back in its rightful place between Dean’s legs.

Stream after stream came out of Cas. Most of it getting into the cup but some of it hitting just on the outside, dampening his fingers. Dean watched little rivulets roll down Cas’ small hands and wrist and nearly went out of his mind.

“God, Cas, so perfect like this. Fuck anybody who can’t see it. Little cow like you walkin’ around outta be proud of what he can do. Makin’ milk, being such a good, big boy. Having small, perky titties. Doesn’t matter if the other boys aint like you. It’s their loss, you’re fuckin’ perfect.”

“Th-thank you, Dean,” Castiel stammered. Of course he was blushing again, but this time it seemed to be more from pleasure than painful embarrassment. Maybe Castiel got off on embarrassment. Dean made a mental note to research this further as soon as possible.

“That’s right, little cow. Perfect just the way you are. You feelin’ better, Cas? These little tits feelin’ better now that they don’t have all that milk pent up inside?” Dean ended his question with a grunt, working through a stubborn couple of passes. He applied more pressure, certain there was more milk to get out, and wondered if he’d end up leaving bruises on his little cow. He hoped not, wouldn’t want anything to mar his perfect baby.

 “Yes, yes, Dean, th-than-nk you!” Castiel was gasping and panting, obviously starting to really enjoy Dean’s efforts.

“You’re welcome, baby. It’s okay if I call you baby while we’re doing this, right, Cas? It’s just that you’re such a little cow still, and you smell so good, just like a little baby all sweet with milk. It’s not a bad thing, right Cas? Do you like it?”

Castiel whined and nodded his head in a vigorous yes.

“Talk to me, Cas. Do you like it?”

“Yes, Dean,” he practically hissed. “I fucking like it.”

“Such a naughty, little mouth, Cas,” he said, fingers slipping to his milky nipple and tugging on the nub. He didn’t say anything else though, but he didn’t have to, Castiel started whining again and Dean slid his fingers back up, rubbing his thumb up and down soothingly.

“Almost done here, baby cow. Gonna feel like a new little cow when I’m done.”

Dean needed to hurry up and either get Castiel out of the classroom or say fuck it and bend the boy over the desk and start fucking him. He _needed_ to come.

He worked the tit over, applying steady pressure and rolling the channel back and forth. Castiel’s head fell back, his eyes closed, whimpering. Dean admired his lashes, the curve of his nose and the swell of his lips. They actually looked kinda chapped. He would enjoy chafing them further.

Cas’ hands started lowering and Dean started missing the cup, but neither of them cared.

“There ya go, baby. There ya go,” Dean said, pumping out the last bit.

“Such a full little cow, udders all swollen. But not anymore, baby. Should be able to fit em back in that little bra you’ve been wearing.” Dean gave Cas’s tits one last squeeze. They were slick from the milk they’d spilled everywhere. Too small to push together and fuck but maybe someday they’d be big enough. Dean shuddered and stepped away.

Castiel’s eyes popped back open, his tail swished between Dean’s legs one last time before he stepped away, pulling the damp cups back over his breasts.

“Th-thank you, Mr. Winchester,” he said quickly, hurriedly putting the cup down and his shirt back on, still keeping his back to Dean. He knelt down to pick up his hoodie and backpack, ears flickering back and forth wildly, and then practically ran out of the classroom without looking back.

Dean was sad to see him go so quickly but also felt relieved. Grabbing the cup full of Castiel’s precious, frothy cream he strode over to the door as fast as he could, slammed it shut and immediately pressed his back against it, hand already digging into his pants. Not even bothering to take his cock out of his briefs Dean started pumping furiously, palming the glands and then stripping his hand down the length, his dick slick with pre-come. He brought his hand out once to spit into the palm and then pushed it back and started fucking his fist. As he felt his come rising he impulsively brought the cup to his lips and drank. Warm, sweet milk spilled down his mouth as he bucked into his hand, making a mess in his pants.

**Notes for the Chapter:**

> As always, feel free to prompt. I've got my fair share of squicks (believe it or not), but you never know. It might inspire!


	3. Chapter 3

**Notes for the Chapter:**

> Ugh, I'm sorry. I tried writing this entire bit from Cas' pov, and I freaking hated it. So I'm putting up the plotty part that somehow snuck into this story while finishing up the structural rewriting of the porn part. So if you're here just for porn my sincerest apologies, but the next two chapters will make up for this. From here on out I solemnly swear to only write PWP. 
> 
> Next chapter with some porny goodness should be up very soon. 
> 
> Also, I was blown away by the response for this story. Thank you so much for taking time out of your day and leaving a comment or hitting the kudos/bookmarking/reading - it's nice to write stuff and have other people like it. :)

After Dean milked him Castiel had run into the bathroom, slammed the stall closed and proceeded to try to scrub his come off of the inside of his briefs. He couldn’t fucking believe it: he had actually ejaculated while Mr. Winchester milked him. His face was burning from shame. He finally said fuck it, stripped his pants and undies off, then balled up the briefs and threw them into his backpack. There wasn’t too much he could do about the front of his jeans, but they weren’t too bad. His chest had been pretty damp, but he patted off as much as he could before starting the long walk home.

Since then he had come an innumerable amount of times to just the memory of Dean Winchester  calling him baby, let alone the way his big hands had felt on his tiny boobs, or the way he had told him he was perfect, or how good his lips looked while he licked them. Cas had even jerked off a few guilty times remembering what Dean’s hands looked like covered in milk, squeezing his breasts and calling him little cow. Castiel knew what they were doing was wrong, he fucking knew it from the beginning. But he was no more capable of stopping it then from convincing the sun not to rise. Dean probably didn’t know how bad it was to let a practical stranger milk him, let alone how truly awful it was to get off on it. Castiel slumped: he had probably just bought himself an express ticket to hell.

But it was _Mr. Winchester_. The man had been fueling Cas’ fantasies and wet dreams since he’d freaking enrolled at the damn school. The way the man pursed his lips when he was thinking, rested his hands on his hips while talking, crinkled his eyes when he laughed… he was so hot it physically hurt Castiel.

Sometimes, when Castiel was tweaking his nipples or pulling on his dick or rubbing at his pucker, he would let himself fantasize that Dean Winchester actually wanted him back the same way. He would constantly replay their encounter, turning over certain phrases again and again. Sometimes Castiel would let himself believe that his pants were from arousal and not because he was straining because Cas’ tits were, “stubborn” or “naughty.” Or that when Dean had asked to call him baby it was because he liked him, and not because he thought of him as juvenile or just some kid.

It had been five whole days since Dean had helped him, and Castiel, too embarrassed and shy to make any kind of indication that he and Dean and done anything, kept his eyes glued to the desk, hoping and dreading that Dean would make some kind of move, bring it back up. But if the man had thought anything about their after school activity he didn’t say anything to Cas.

He probably regretted it, Castiel thought. He figured that Dean knew how turned on he had been and thought he was some kind of major freak. And then Castiel wanted to die from mortification when he wondered if Dean knew he had come. He was surprised the man hadn’t had him removed from his class yet.

Worst of all, Casitel’s tits were filling with too much milk again. He had tried _so many times_ to do it on his own, but hardly anything came out. He had even watched some terribly embarrassing and poorly produced instructional videos from the _Proud to be Cow_ YouTube channel. They were starting to get kinda painful, and Castiel was scared there was something wrong with them, and that he’d have to go to a doctor and get them removed - a thought that sent him into severe panic.

After another failed attempt at expressing his milk Castiel got so frustrated he tore up his room and spent the next hour crying. The love of his life, his freaking teacher, thought he was a perverted freak. His parents were fucking clueless. He hadn’t made any friends at his strange, new high school, he missed his old friends, douche bags at school made fun of him for being different,  and now his tits hurt because he couldn’t fucking milk himself like a damn adult.

All in all, Castiel found himself to be pretty fucking broken.

 

Castiel stopped by a store on his way home one day with the intention of buying a breast pump. He hadn’t heard of any other Cows using one, but he figured desperate, pathetic times and all. After checking down the aisle to see if anybody he knew was around, Castiel darted over to the pumps and quickly scanned for a mid range one. It was far more expensive than he had counted on, but it was a bit of a necessity so he grabbed it and left. However, on the way to the register he cut through the women’s clothing section and saw something that caught his eye: a beautiful, pale pink, lacy bra. Castiel stared at it for a few moments before taking a few sheepish steps and running a finger over the fabric. It wasn’t as smooth as he thought it would be, but it was unlike anything he’d ever seen. 

He imagined himself in it, imagined Mr. Winchester seeing him in it, and immediately grew bright red and nabbed it. Then he checked the price. It wasn’t as much as the pump, but together they were both more than he could afford.

Castiel debated, he knew he should buy the pump. He needed to buy the pump. But the bra was so pretty and delicate…

 

The next day Castiel walked around all day with his hoodie up. Mr. Winchester had barely even acknowledged him in class, and he had been looking so sexy too. Castiel loved it when he wore a particular pair of dark jeans. Plus some of the dickbags in gym had started tugging on his tail and asking him for milk, but he did his best to ignore them and stay out of trouble. He wondered how much longer he’d have to put up with this crap before his parents would let him go back to his old school. 

Class had been out for about twenty minutes, and Castiel was on his way home, when he remembered that he forgot a textbook and had to swing back and grab it from his locker. He kept his eyes and ears on alert as he walked down the hall and discreetly rubbed at his tits. It didn’t make the pain go away completely, but it helped give him some relief.

As he rounded the corner he stopped just short of Dean’s door. It was halfway open and he heard two voices: Dean and that damn catboy. He’d been flirting with Mr. Winchester all week, wearing tight shirts and booty shorts, purposefully dropping pens and picking them up while Mr. Wincehster was lecturing… _yowling_. And his scent, Jesus, he must be about to hit his heat because it was nauseatingly sweet. His actions made Castiel sick. And terribly jealous. What if catboys were Dean’s type? After all, Gordon was very pretty.  And catboys were very in right now. Maybe Dean was one of those humans who didn’t discriminate between sentients.

“Come on, _Mr. Winchester_ , don’t you want to see how much of a naughty kitty I can be. Just let me suck you off. I bet you’ve got a huge cock.”

Castiel’s stomach started tying in knots. This was it, the moment he would finally have to accept that Dean Winchester wasn’t into him; the moment his heart would actually break.

“I’m sorry, Gordon. You’re a very, very attractive boy. I’m just not… in the right place right now to take you up on your offer.”

Castiel’s breath hitched.

“But, Dean,” the catboy wailed.

“Please., Gordon, it’s Mr. Winchester, remember? Gotta have some semblance of authority, right, kid?”

Castiel clapped his hands over his mouth. He wanted to cry and laugh and cry some more he was so happy.

“Now I’ve gotta go, got some plans I can’t miss, but don’t worry about this, Gordon. You can easily find somebody to help you out with your heat. Somebody with more stamina-“

Castiel didn’t hear the rest, because he had heard them walking closer to the door and not knowing what to do, he ran to the bathroom. He would just wait it out in there until it was safe to go out to his locker and grab his book.

He tried scrolling through his facebook and instagram, but he was too preoccupied. What did that mean, letting Castiel call him Dean but not Gordon? Did he see Castiel as an exception? An exemplary student? Something else, something more? Cas tried to shoot down any hope that Mr. Winchester could be into him, but it didn’t stop some of the joy from seeping through either: at least he wasn’t fucking Gordon.

Castiel left the bathroom a few minutes later. Dean’s door was closed and the lights were off, so he figured it was safe to go and grab what he needed. As he was working the combination to he heard somebody clear their throat.

“Heya, Cas.”

Castiel’s body froze, but his ears and tail twitched violently before he turned around.

“Mr. Winchester,” he stammered, leaning his back against his locker but not looking up.

“Cas- did I… are we okay?”

“We?” Castiel asked, tilting his head and finally looking up at his teacher. Dean was beautiful. Somehow Castiel always forgot how pretty he was. Especially now, with a slight stubble on his jaw, his collar unbuttoned, eyebrows furrowed.

“Yeah, I mean… are you – did I hurt you, Cas?”

“Wh-“ Cas frowned, “hurt me? How?”

“Cas,” Dean let out a frustrated sigh and ran his fingers through his hair. “Last week, when I,” he gestured at Castiel’s breasts, “did I hurt you? Did I make you feel bad?”

Castiel felt conflicted. He had a large amount of guilt over what they did. On the other hand he had also produced a large amount of come. He looked down and scratched his head, right behind his ear.

“No,” he finally said. “No… you didn’t hurt me.”

“Yeah?”

Cas nodded.

“So why can’t you look at me?”

Castiel glanced up and then looked right back down and shook his head.

“Is it because I did something wrong? Look, Cas, if you think I’m some kinda creep, some kinda asshole, you gotta tell me. Or tell your Mom and Dad, or the principal. I can’t have you torturing yourself by staying in my class because you’re scared I’ll be mad at you, or lie about you. I’ll own up to it, I swear. I just want you to be okay.”

Castiel felt his chin quiver. He was completely overrun by emotions. He wanted to launch himself into Dean’s arms, and hug him, and tell him it would be okay, that he could never hate him. Instead he managed to look Dean in the eyes and shake his head no. He could feel his eyes brimming with tears. He thought he must look like a pathetic baby to his teacher.

“Hey, hey, none of that, Cas,” Dean said as he cupped his face with both hands and ran his thumbs over Cas’ cheeks. “It’s okay, Castiel. You’re okay.”

Castiel nodded and tried to smile.

“So, you don’t hate me?”

“No,” Castiel said as he shook his head. His tail wrapped around his own leg, trying to get as much comfort as possible.

“That’s good.” Dean smiled, and it lit up his entire face. Castiel smiled back, unable to help himself. His face burned where Mr. Winchester was still touching him. He was sure Dean could see.

“Well then, if you don’t hate me, have you been avoiding me because you’re embarrassed?”

Castiel’s eyes dropped, and he nodded his head ever so slightly.

“Well that’s no good, Cas. You’re my favorite student. Can’t have you trying to dodge me left and right just because I helped you with a problem. It’s what teachers do.”

Dean smiled again and dropped his hands to Cas’ shoulders. Castiel felt goosebumps form all over his skin.

“So, how is the problem, Cas? Figure out how to milk yourself yet?”

Castiel’s mouth was dry, but he swallowed as best he could and managed a soft, “No, Mr. Winchester.”

“Please, Cas. Call me Dean?”

He felt Dean’s thumbs moving up and down and he wanted to lean into the man’s touch, get those hands everywhere else.

Cas nodded yes in response to Dean.

“So… did you need any more help, Castiel?”

Castiel felt his eyes grow big. He should have known Dean would offer again, and yet it was still a surprise to hear the man say it. Castiel quickly nodded his head.

“Gotta say it, baby.”

Castiel immediately flushed at the endearment but was able to make himself say, “I need you to milk my udders, Dean.”

Castiel felt a rush of guilt as soon as he said it, but there wasn’t a force on this earth that could make him take it back either. Express ticket to hell be damned.  

 Dean closed his eyes and smiled, but the next thing Castiel knew Dean had taken a step closer and was unzipping his hoodie.

Castiel wanted to panic, to tell him no, not in the hallway, but he was transfixed by Dean wetting his lips. He felt his tongue dart out and wet his own too.

Dean let out a low whistle as he cupped Castiel’s tits. They were so full again. Castiel arched his back into Mr. Winchester’s touch, putting relief ahead of his fear of being caught. Dean’s fingers felt fucking perfect. They were so big. Dean swiped a thumb over Castiel’s nipples and he could feel them start to harden. He suppressed a shudder.

Dean’s hands trailed down Castiel’s chest down to stomach, making the calfboy whimper at the loss of contact from where he wanted it the most. Dean’s mouth quirked into a smile as he took one of Castiel’s hands in his own. The hand was big and warm, and Castiel loved the way it felt in his own, and the way his stomach kept swooping in circles. Dean gave Cas’ hand a little squeeze before turning around and leading him into the classroom, hand still engulfing his own.


	4. Chapter 4

As soon as they were inside Dean shut the door and was up in Castiel’s space. He breathed in deeply and sighed. His little cow wasn’t mad at him. And he was about to get in another milking. Life had suddenly gotten much sunnier.

Dean pushed Cas’ hoodie down so that it pooled on the floor and then put his hands on the hem of Castiel’s shirt. Dean relished in the fact that Castiel’s breath hitched and that his tail and ears started twitching again. A very good sign.

“Dean,” Castiel responded, but Dean shushed him with a finger to the mouth that he rubbed up and down his lips a few times. He couldn’t help it, they were just so soft and warm. He could feel Castiel shuddered, so Dean slowly put his hand back down and lifted Cas’ top off.

And then he gasped.

Cupping Castiel’s taut udders was a lacy, light pink bra. Dean could see Castiel’s nipples poking through the fabric, and he moved out a finger to trace over them.

 “So beautiful, Cas. Did you buy this just for me?”

Dean loved the way the boy looked so shocked. Apparently Dean had guessed correctly.

“It’s okay if you did, baby cow. Just look at you. You’re so fucking precious.”

Cas felt his face burning. He tried to bring his hands back up to hide himself from Dean, but the older man caught them and brought them back down. Dean wasn’t going to let Castiel hide this beautiful sight from him. The boy looked fucking delicious.

“None of that, little cow. I thought we were over that. Good little cows don’t hide their pretty, little titties from their teachers. They show them off like big Cows. You want to be a big Cow, right, Cas?”

Dean silently cursed himself for already slipping back into this roll, but he couldn’t help himself. Plus, it appeared that Castiel didn’t mind either.

In fact, Cas’ stomach flipped with embarrassment and arousal. He’d never heard anybody talk the way Mr. Winchester did. It made him feel so funny, like he wanted to hide and explode at the same time. Unable to verbalize a response, he settled on nodding and kept his balled up fists down at his hips. He watched Dean’s eyes rake over his body, lingering at his hips this time before bringing them back up to his face. As soon as Dean made eye contact Castiel blinked and looked away. It was too much for him.

“How do you want to do this, Cas? Like last time? Or do I get to look at that gorgeous face while I milk these titties?” and while saying that he put his hands back on Cas’ breasts and gave them a squeeze.

“F-front is fine,” Cas stammered.

“Perfect. Now, these little udders aren’t so little right now, are they, Cas?”

Castiel shook his head.

“And why is that?”

“Be-because they’re full of milk, M- Dean.”

“That’s right, baby. So swollen, so sore, they need to be expressed. And if you can’t do that you need to find somebody who can. Do you know anybody that can do this for you, Castiel?” Dean asked, flicking a nipple through the cup. It caused a strange sensation to run through Cas like electricity. Castiel felt his pucker do something weird, but he wasn’t sure what.

“Y-you can, Dean.”

“That’s right, buddy. I can. So why didn’t you come and get me as soon as you needed help? Is it because you’re a naughty little cow? A bad, little boy who needs to be punished?”

Castiel’s head jerked up and his lips started trembling. It looked like he was about to cry. Dean’s heart clenched, he hadn’t meant to upset the boy. He was just teasing the waters, seeing what turned the kid on.

“Hey, hey, hey,” Dean said, tone changing entirely. He swept Castiel into his arms and hugged him tightly, relishing the way his tits squished against his body.

“It’s okay, baby doll. I know you’re not a bad cow. I was just teasing you. I know you’re a good calfboy who was too embarrassed to ask me to make him feel better. But it’s okay. I’m gonna make you feel real good, baby. I’m gonna make you feel so much better. Do you trust me, Cas?”

Castiel let out a tiny hiccup as he nodded. He felt kind of strange, letting a grown man hold him while he was only wearing a bra, but it also felt really good. Dean’s hands started rubbing on his lower back, fingers just brushing the base of his tail. And his stubble felt scratchy against Castiel’s cheek, but in a nice way.

“Alright there, buddy. Let’s get you milked.”

Dean must have unhooked his bra while his hands were around his back, because as Castiel pulled away he felt the shoulder straps slide off and the bra fall down some. With a finger Dean finished dragging it all the way off, and Castiel immediately felt exposed. But he kept his hands down just like Mr. Winchester told him to. He glanced up at Dean’s face, watched his nostrils flare and then brought his eyes down to Dean’s lips.

Dean caught the movement and suppressed a smirk. The boy wasn’t exactly being subtle. Dean figured if he acted with caution he’d be able to get a bit further than last time.

“There we go, little cow. See? Probably feel better already with that bra off. It’s really cute though. You look really pretty in it.”

Castiel blushed. Boys weren’t supposed to look pretty. Cows didn’t even wear bras. It was just that everybody had kept staring at him.

“Thank you, Dean,” Cas responded, deciding to accept the complement instead of explain away why it wasn’t in fact cute or pretty. Then Dean started kneading his breasts, and he let out a low moan. He couldn’t help himself. It felt so good. Dean really knew what he was doing.

“Bet all the boys were happy to see you lookin’ like this today.”

Castiel frowned. That was the exact opposite of the truth.

“None of them saw me with it. I change in the bathroom.”

Dean’s breath hitched, but he kept on massaging Castiel. The calf really had bought the bra just with him in mind. Dean felt his dick start filling out and shifted on his feet.

He would take breaks from massaging to run fingers under Cas’ boobs and then back up, rubbing over the nipples and tugging on the ends a bit, playing around. He wanted to get Castiel used to his touch. The boy had his eyes closed and he was biting his bottom lip. Dean wanted to see Castiel’s big, blue eyes opened and glazed over in pleasure so badly, but he could wait.

Castiel hadn’t been able to maintain eye contact with Dean while he was fondling him, but he knew his ears were pointed forward, absorbing any tiny little sound that his teacher might make while getting his breasts warmed up for the milking. He filed away every sigh, every huff of air, intending to use them later while he was alone.

“You ready to get this milk out, baby boy?”

Castiel nodded and then hissed as Dean rolled a nipple a bit too roughly between his fingers.

“Sorry, Cas. Didn’t mean to hurt you!”

“It’s okay. Uhm… should we get a cup?”

Dean almost told the truth, but then another brilliant idea struck him.

“Don’t have one today. Gonna have to get milk all over this floor I guess,” Dean said. “Maybe we could use your shirt to soak it up? You could just wring it out after and either put it back on or throw it in your backpack and wear your hoodie? Doubt anybody would even notice,” he suggested.

Dean thought Castiel looked like he was about to object, so he started working Cas’ tit and a solid stream of milk shot out, hitting Dean square in the chest. Dean wanted to moan as the warm liquid soaked through his shirt, but he kept his mouth shut.

“Oh-oh, my god, Mr. Winchester. I’m so sorry!” Castiel sounded mortified.

“It’s okay, Cas. It was my own fault. Now why don’t you hold up that shirt so I can squirt this milk onto it?”

Castiel placed the shirt right in front of his nipple, and Dean started milking his udders. Castiel knew his face was still red, he couldn’t believe he was being milked into his own shirt. But he was doing what Dean asked, and Dean was super smart so he knew what he was talking about. Castiel felt his fingers roll forward to his nipple and wished that they would keep going and squeeze the ends again. He really liked when Mr. Winchester did that, it made him want to arch his back and moan. But Dean was a professional, only doing a job. Still, Cas felt his dick getting harder as Dean kept on working him. He was a lot quieter than last time, and Castiel sighed with sadness. Apparently Dean would be withholding all of those beautiful words from him this time.

A few times Castiel would look up at Dean and he would be staring intently at what he was doing, not sparing Cas any of his attention, but once or twice Dean had been looking straight at him, and Castiel could feel his insides melting into puddles of goo. His eyes were such a beautiful shade of green, even if most of the iris was being obscured by his pupils. He looked so serious, so intense. It terrified Castiel to his core, while delighting him with some unknown sensation as well. He quickly looked past Dean, over the man’s shoulders and unfocused his eyes, just letting himself feel Dean’s fingers, strong and warm, moving over his skin.

Dean had been doing his best to keep his mouth shut, waiting for Castiel to get more comfortable with what they were doing. But the feel of his breast starting to get too slicked up from his own milk was too much. Dean looked down at the boy’s udders, so beautifully pale and nipples so painfully hard, standing so perfectly and taking what Dean gave him. It made his heart swell with pride.

“Jesus, just look at you,” he said as he made another stream jet out of Castiel’s nipple. “So good for me. Such a good Cow. Such a grown up boy, letting me milk his little udders while he stands up so good and still. Can’t look me in the eyes, not yet, baby, but you should. With tits this perfect, with your gorgeous mouth and sexy bra. Jesus, Cas. I had no idea. No idea you liked it. Thought you hated it, in fact. But then I saw this bra. This perfect fucking bra that you went out and bought and, just, Jesus, you’re so fucking perfect.”

Castiel stammered, and started fidgeting with his belt loops. Dean observed the movement and decided to comment.

“You’re nervous again, baby?” Dean asked, eyes flicking down to Castiel’s pants, wanting to see if his hunch was correct. Castiel immediately shot his hands down to cover his dick, but it was too late. He looked back up, expecting Dean to shove him away any second.

Instead Dean was smirking. The boy really did get off on all of this.

“Jesus, Cas. You really _do_ like it.” He pulled extra hard on Cas’ udder, and Cas wanted to scream and run away and hide forever. Instead he just squirmed.

Dean rested his hands on Cas’ shoulders and settled his movements.

“It’s okay, Cas. That’s natural too. Anybody ever touch these udders before? I mean for fun?”

Castiel shook his head.

Dean wasn’t all that surprised. The boy was so damn shy about all of this. And yet the idea of being the first man to play with such a beautiful creature… Dean felt a ball of pre-come push out of his dick.

“Christ. Just me, baby? Fuck.” Dean bit his lip. Castiel wondered if that was a good thing or a bad thing.

“You like having these little titties played with, Cas? Tell the truth.”

Castiel nodded.

“Use your words, baby.”

“I-I like having my titties played with.”

Castiel felt white hot shame rocket through his core. He wasn’t supposed to like this, and yet he had to bite back a groan. Dean’s words were starting to make his dick ache for touch.

“Yeah? Cute, little cow like you – you’re of age. Why haven’t you had anybody play with them for you then?”

Castiel shook his head and said, “No-nobody ever wants to.” He bit his lip and tried blinking his eyes several times, determined not to cry in front of Dean again.

Dean almost had him say it again. There was no way he had heard that correctly. Castiel was so sexy, and he didn’t even know it.

“Nobody ever wants to? Now, baby, you know that can’t be true. I bet there’s tons of people and ‘brids who would give anything for a chance at these sweet tits. Keep holding the shirt up, baby.”

 It was getting heavy from milk and Castiel had unintentionally started lowering his arms.

“That’s right, that’s good, right up against that tit so it can soak up all your sweet cream. Shame to lose all that cream though, baby. Maybe we could find something else?”

Dean arched an eyebrow and licked his lips. Castiel blanched. Did he really mean what Castiel thought he meant? Of course not. That would be obscene. And yet Castiel couldn’t ignore the tight, pleasant feeling low in his gut when he pictured it. Dean noticed that his tail gave a solid swish before going straight again.

“Alright now, baby. Gotta switch tits. This one’s all outta your milk,” Dean said, giving it a playful jostle. “Feels better though, right?”

“Yes, Dean,” he mumbled.

Dean took a step back. “Damn, Cas. When you look at ‘em you can really see the difference. This left one is so full, so swollen. Just aching for me to milk that sweet little tit, aren’t you, Cas?”

Castiel blushed but nodded his head.

 “That’s right. You’re so pretty when you blush, you know that, Cas?” Castiel shook his head.

“No? Well, it’s true. Know what else is true? I like making you blush.”

 Castiel bit back a smile.

“You get real embarrassed sometimes though, huh? Well that’s okay. Though little cows like you seem to get awfully turned on when they’re embarrassed.”

Dean stepped back in to Cas and started working Castiel’s other tit. Dean could tell Castiel had been fighting back his moaning but he slipped up and let out a tiny groan while pushing his chest out for Dean. He felt the tinges of embarrassment around the pleasure of having Dean’s hands on him, and it was as if Dean could read his mind.

“I know, baby. I know. It’s okay. Like I said, it’s part of life. Young guy like you is bound to like being touched. Perfectly natural for the body to react this way.  I don’t remember the first time I got hard, but I do remember the first time I popped a boner in public. It was my first grade teacher. She was a beautiful bunnygirl. She had nice hair, pretty face… a beautiful, big ass. I remember she was leaning over to check on whatever stupid shit we were doing in class, probably drawing butterflies or some shit, and I realized I could see down her t-shirt. She was wearing a dark bra, probably black, and I couldn’t even really see ‘nothin, some cleavage but not even the sliver of a nipple, but I popped wood right then and there. I was so embarrassed I wasn’t sure what to do. But, you know what I did, baby?”

Dean asked as he kept his fingers moving up and Down Cas’s tit, working it almost like a cock.

Castiel shook his head, absolutely enthralled.

“I went into the bathroom and played with it until it went away. When I got back all the kids thought I had taken a huge dump and didn’t stop teasing me for weeks.”

Despite the charged atmosphere, Castiel laughed. He also felt a little bit better about his current situation. Dean was glad to see that smile again.

“Anyways,” Dean said after chuckling, fingers still moving Cas’ tit back and forth, “how ‘bout you? You ever jerk yourself off?

Castiel nearly choked on his surprise. It was bad enough he had a raging hard on while doing this, that Dean had told him he looked nice in the bra or that he had masturbated in a school bathroom when he was young, but for Castiel to describe his intimate sexual moments while being milked? There was no way he could do that.

Dean saw the panic coming back and quickly tried to soothe it down. “It’s okay if you do, you know? Not sure how conservative Cows are, but everybody does it. Anyone who tells you different is a miserable liar.”

Dean bit his lip, waiting to see if Castiel would take the bait.

Castiel, while finally making eye contact with Dean, slowly nodded his head yes.

Dean almost groaned out loud.

“Yeah, baby, you like jerking that cute, little cock of yours I can see tenting in those jeans?”

Castiel whimpered.

“Or do you like working yourself open and having something nice and big stretch you wide?”

Castiel’s eyes got huge, and he quickly shook his head no. Dean breathed deeply. There was so much he was going to be able to teach his little cow.

“Aw, baby. Not even a little bit? You ever rub at your hole, let a little bit of finger slip in? Hell, baby cow, everybody likes that. From big ole Bulls to the cutest little fox girls. There’s so many nerve endings there, it feels so good.”

Dean leaned in, keeping his hands still pumping Cas’ tit, and whispered, “even boring, old humans like me like it.”

Castiel moaned, unable to stop himself. Dean took a step in and took a whiff of his neck, rubbing his nose lightly against the skin.

Castiel’s hands sprung up to Dean’s shoulders and held on to him, neither bringing him forward nor pushing him away. He wasn’t sure what he wanted, he felt like he was going to explode. The only thing he did know was that his dick was dying to be touched. Neither of them had noticed that he had dropped the shirt.

“Bet you’ve got such a sweet, cute hole, baby cow. Cute little hole to match these perfect baby titties.”

And suddenly Dean could feel it, Castiel had pressed his crotch up against Dean’s hip and rubbed his dick against him. Just as quickly Dean had pushed Castiel against the door and started sucking on his neck, hands no longer working his tits for milk.

Castiel moaned and started humping Dean’s thigh with little coordination. Dean loved how short and stiff his cock was. He  used his teeth to nip Castiel’s neck before moving his mouth up to finally kiss Castiel’s panting mouth. One hand went up to the boy’s hair, grabbing an ear as well, while another cupped his ass, pulling him in even closer. Castiel accepted Dean’s tongue in his mouth, letting the older man lead the way.

Dean groaned as his tongue played over Castiel’s. The boy was so pliant, so accepting. He gave the boy once more kiss and then started mouthing at his lower neck and collar bone.

Castiel began to whine when Dean took a step back and trailed a finger over the boy’s bulge.

“Such a cute bulge you’ve got for me, little calf. Can I open it up and play with your little, cow cock?”

Castiel ground his crotch into Dean’s hand in response and tried to bring the man’s face back to his own for more kissing, but Dean had other things in mind.

He licked up the middle of the boy’s breast bone while undoing his button and zipper, and Castiel gasped. The calfboy tasted so sweet, his milk had gotten all over his chest, but Dean was certain he had more. Dean looked down and almost laughed. He had been expecting cute pink panties to match the bra, but instead Cas was wearing black briefs. It was still hot, seeing his stiff prick straining against the underwear, just not what Dean expected.

“Didn’t get the matching set, huh, baby cow?”

Castiel blushed like mad, looking away and biting his lip.

Dean leaned back in and kissed him soundly on the lips.

“It’s okay, Cas. You still look so fucking sexy. Love seeing you like this, baby. Such a shy, quiet little cow in class. Always sitting up straight and doing his work like a good calfboy. Now look at you, covered in your own sweet milk, moaning and panting like a good, little boy, briefs soaked in pre-come. You love this, don’t you Cas? You love being a good, little, baby slut and getting these pesky udders milked by teacher, don’t you? Got your nipples red, gonna be feeling me tomorrow while your tits press against one of your tight, little bras, I can promise you that.”

Castiel groaned in response. He’d never thought of himself as a slut before. But he would be anything, do anything, if it meant getting Mr. Winchester to touch his dick again. It had been feeling so good, but now it was aching.

“Pl-please, Dean,” Cas panted.

“Please, baby cow? Please what?”

Castiel’s ears fluttered.

“Please, please touch me again. I’ll do anything, please. Please!”

“Okay, baby, I got you, I got you.” Dean palmed at Castiel’s erection and then started kissing at his collarbone again. Castiel felt that same strange feeling down at his hole – like it was trying to grab on to something.

Then, in one swift motion, one of Dean’s hands went to Castiel’s shoulder while the other held one of Cas’s hands down at his hips, and he started kissing on Cas’ boobs. They were so soft and perfect, but Dean kept away from the nipple, wanting to wait just a little bit longer.

Castiel went red with shame but he didn’t tell Dean to stop. It felt so good. He even liked the way Dean was holding him down, instead of feeling scared he felt safe. He started bucking into the air, craving friction against his cock.

Dean could feel Cas moving, so he dropped a hand from his hip and started rubbing the boy’s dick harder and encouraging Castiel.

“Come on, little calfboy. Look so good fucking into your teacher’s hand. You were made for his, baby boy. Such a good cock you’re growing, just like these perfect udders. Gonna be such a good cow slut, baby. Fuck, you look so good.”

Castiel groaned at the praise and started rubbing against Dean’s hands with vigor, wishing Dean would just reach into his pants and grab his dick. But since he hadn’t offered Castiel didn’t ask.

Cas’ thrusts were getting erratic and Dean couldn’t stop himself. After telling Cas he looked good Dean bent down and licked a broad stripe over one of Castiel’s nipple. Castiel’s back went ramrod straight and Dean did it to the other. The boy made the tiniest gasp and Dean latched on to a tit, sucking on the udder for all he was worth. He felt Castiel’s spunk spill white hot on his hands through the briefs. Dean moaned and pushed into Castiel harder. He brought a hand up to Castiel’s tiny titty and started working it for milk which began flooding his mouth. It was the sweetest thing he had ever tasted.

Castiel’s hands shot to Dean’s head, but he didn’t pull the man off. He could feel Dean milking his breast, drinking his milk down while his hand slipped down past Castiel’s waist band and groped his bare ass.  His fingers dipped into Castiel’s cleft, and one barely touched his furled opening before Castiel hissed and started babbling.

“Oh, Dean, oh, oh, my god. Dean. Dean, you can’t do this. Dean, you- this is, oh, my god. Dean, Feels so good!”

Dean started sucking from his udder earnestly. Swallowing down as much of Castiel as he could. Between being latched on to his tit and a hand squeezing Castiel’s perfect ass, Dean was in heaven.  Castiel’s head fell back against the wall. His cheeks were burning red.

“Fuck, Dean – Mr. Winchester! Fuck! This is so bad, god, this is so bad. Fuck, god, feels, ah, feels good!”

Dean moved his hand to Castiel’s front and rubbed at Castiel’s deflated dick, and the boy started sobbing.

“Please, please, Dean. No more, I –too much, I can’t-“

Dean pulled down Castiel’s pants and underwear a bit more and then knelt down. Castiel’s spent dick was totally exposed, and Castiel wanted to cry from humiliation.

Dean looked up at him though, and the reverence in the man’s eyes went over him like a cool balm.

“So perfect like this, Cas. Tits all a mess from my hands and my mouth, milk running down your stomach, come clinging to your little dick and balls and lower tummy. Always want you like this, baby. Always.”

Castiel groaned and shut his eyes, he couldn’t handle looking at Dean looking at him like that anymore.

“Gonna taste you just a little bit more, baby,” and with that Dean started licking up the come that was still left on Cas’ body. With slow, heavy licks he cleaned his thighs and trail. With soft little kitten swipes he cleaned his shaft and sack, gently sucking a ball into his mouth, then the other. Castiel was gently squirming, trying to get away from Dean and then trying to get even closer. Dean doubted he even knew what he was doing.  Dean went up and licked a rivulet of milk off Castiel’s stomach before going back down and cleaning up more come.

Castiel looked down and felt his dick twitch at the sight. Dean fucking Winchester was on his knees, licking up his own come and milk off his own stomach. He still felt a little embarrassed, he was just a scrawny kid. But Dean was treating him like something else entirely, something important, special. Not like something broken or dirty or wrong. Castiel moaned again and Dean looked up and smiled.

“There’s my perfect, little cow.” He gave Castiel’s dick a quick kiss and then stood, grabbing Castiel’s hoodie on his way up.

Dean kissed Castiel soundly on the lips one more time and then helped him into his hoodie. Castiel tucked himself back into his jeans and then silently looked up at Dean.

Dean, maintaining eye contact, slowly zipped up Cas’ hoodie.

“Mind if I keep this?” Dean asked, bending down and then swinging the bra by its strap on his index finger.

“I’ll give it back, I promise.”

Castiel had no idea what Dean wanted to do with a bra, but he nodded his head yes. Of course he nodded his head yes. Like he had said, he’d do anything for Dean.


	5. Chapter 5

**Notes for the Chapter:**

> Well... this 5k fic has somehow turned into another ginormous monster. One more chapter, guys. But I think before that I'm gonna write a wincest prompt because someone is a very bad person who took advantage of a naive little smut peddler! Just kidding.  
> Mostly.
> 
> Anyways. I have a tumblr if you feel like prompting me or sending me Cas porn. Or Dean porn. Preferable all of the above. Still--ill with two dashes because the pickin's were slim. (Word to the wise it's nsfw, and I'm too lazy to tag for that. If you don't want gifs of dick on your dash don't follow.)
> 
> Also I threw up some prompts at spn kink meme go fill them I don't want to do all the work!

Castiel had ended up walking home after fooling around with Dean. As the two were in the bathroom, rinsing and ringing out Castiel’s shirt, Dean had insistently offered the calfboy a ride home; however, Castiel had waved him off. He had actually wanted to be alone. It wasn’t that he was spiraling into some sort of traumatized depression, but he did have a lot on his mind: he had broken one of the core tenements of his culture, and on top of that he had finally had his first sexual experience with another person. Needless to say, Castiel needed to time to process events on his own, and the walk home had actually helped.

Dean, accepting that Castiel was really going to reject his offer, asked if it was still okay to kiss him goodnight. Castiel’s cheeks went slightly pink and he nodded. At first Dean just brought his hand up to one of the boy’s ears and gently rubbed it, admiring how velvety smooth it was. And then, cupping his face, he gently kissed Cas warm, soft lips. Castiel hummed and Dean gave his bottom lip an extra nibble before sighing and letting him go.  It was only Wednesday, Dean reasoned. He’d still be able to see the calf at least two more times before the weekend.

As Dean walked out to his car, he kept one hand in his pocket, fingering the pretty little lace of Castiel’s new bra. He smiled to himself and thanked the universe that he could think fast on his feet.

 

Castiel sat in Mr. Winchester’s class, occasionally pausing his diligent note taking to appreciate Dean’s beautiful body. Of course Dean caught him staring and would smile every time and on one opportune occasion winked. Castiel felt his face flush, and Dean just smiled harder.

Dean, on the other hand, was quite pleased with himself. He had stayed up late grading papers just for the sole purpose of handing Castiel something back with instructions to see him after class. When the time came Dean started handing out the worksheets. He approached Castiel from behind, loving the way his little, black ears twitched and swiveled back as he approached. He leaned over Cas as he placed the sheet face down and made sure to graze Castiel’s breast with his hand. He saw the boy’s nostrils flare as he was straightening back up and repressed a grin.

“Castiel,” he said with as much authority as he could muster, “you’ll have to see me after class about that.”

And with that he sauntered off to the next student, paying the calfboy no mind.

Castiel was scared he’d actually made a bad grade, but as soon as he turned the page over and saw his A he quickly stuffed the paper into his backpack and took a deep breath.

After the bell had rung and Dean had finally been able to shoo Gordon out of his class, Dean shut his door and turned to Cas. Technically it was his conference period, but nobody ever came in to use it. Castiel walked up to the man, big, blue eyes unwavering. It warmed Dean’s heart that Cas was starting to get bold.

“Got you somethin’, Cas,” Dean said, voice low and sultry.

Castiel tilted his head, not knowing what on earth Dean could be talking about.

Dean just smiled and motioned for Castiel to follow him. He led the boy back to his desk and then rummaged through a big drawer until plopping a plain, brown paper package before Castiel.

“Woulda had it wrapped up nicer but didn’t wanna draw attention to it. It’s just uh, well…” Dean trailed off, hand going to the back of his neck. “It’s just something I thought you’d like. You don’t have to keep it if you don’t want it.”

Castiel finally took his eyes off of Dean and then looked down at the package.

Completely at a loss of what to do or say, he reached out a hand towards the bundle and then looked up at Dean.

“Don’t open it now!” he said in a rush. “That’s for you. For later. For when you get home. Just… don’t open it around anyone else, okay?”

Castiel chuckled and grabbed the package. He carefully slid it into his backpack and then looked up at Dean. Finally he made himself speak.

“Thank you, M- Dean,” and then he shook his head. “You really – you shouldn’t have. I don’t need anything.”

Dean smiled. “It’s not something you need, Cas. Only possibly something you’d want.”

Castiel’s smile faded as he took a step closer to Dean. It was Dean’s turn to gulp.

“Thank you, Mr. Winchester,” Castiel said, as seductively as he could manage. Which, honestly, he wasn’t sure was all that sexy.

“Shit,” came Dean’s quiet reply, lips pursed, eyes suddenly half lidded and looking Castiel up and down.

He grabbed the boy’s hip and pulled him closer. Castiel’s eyes shut and Dean ran his hands up the side’s of Castiel’s chest. Cas was wearing a plain blue v-neck, but it looked so good against his pale skin and dark hair. Castiel stood transfixed as Dean pulled his shirt taut against his breasts.

“Like seeing you show these off for me, little cow.”

Castiel blinked, he hadn’t thought of his clothes as particularly provocative.

Dean wet his lips and then leaned in and gave Castiel a sweet kiss.

“Been thinkin’ ‘bout you all night and all day, Cas.”

“Me too,” Castiel murmured back, leaning his forehead up against Dean’s.

“Touch yourself?”

Castiel’s quick intake of air was followed by a shaky nod as he brought his hand down to his crotch and palmed his dick. Dean’s jaw dropped. He had meant to ask if Cas _had_ touched himself, not command him to do it. However, he was perfectly agreeable to this as well.

“Mmm, so good to me, baby,” Dean hummed as he leaned in and kissed Cas’ neck.

“Do me a favor? Before you go to class?”

Castiel groaned, completely forgetting that he had somewhere to be. Dean, guessing that Cas had forgotten about class, chuckled at the boy.

“Anything,” Cas whispered back.

“Give me some of your cream before you go. Just so I can have something to remind me of you?”

Castiel gasped but nodded his head yes anyways. Dean’s look suddenly got much more intense as he scrambled to grab his mug and lift up the boy’s shirt. He quickly pulled down a cup and started squeezing Cas’ milk into his drink. There wasn’t much, but it was enough to help offset the bitterness of his black coffee.

Both of their hearts were pounding as Dean worked Castiel’s tit. Dean, no longer as concerned about hiding his arousal from Cas, started whispering.

“So, so good for me, Cas. Such a good, little milk cow. Such an obedient, beautiful, perfect little milk cow. Hasn’t even been one day, and you’re already back in my room, willing to give me your perfect cream.”

Then Dean began toying with a nipple, pulling on the puffy nub and then wiggling it with a finger.

“Dean,” Castiel whispered, wondering how he was supposed to just go to gym after this.

“Dean, please, hurry, somebody could be coming.”

“Does that get you off, little cow? Wondering if somebody would walk in right now, see how much of a perfect, little, baby slut you are for getting your tits milked?”

“Dean!” Castiel whined, pushing his chest further.  
Dean smiled, he had already started leaning the signs from Cas.

“Now don’t get too excited, baby slut. Gotta go to class, don’t want any of those other fucking assholes seeing how fucking perfect you are, how you’ve got such a cute, perfect cock and suckable, perfect tits. Be a good boy, Cas. Tuck yourself back in and go on. Tell your teacher you got held up by me, I’ll talk to ‘em after school if you need me to.”

Castiel’s scowl mimicked that of a cat who had just fallen into a giant tub of ice water.

Dean chuckled and ruffled his hair.

“Go on, baby cow. Get to class. And don’t forget your present!”

 

Despite having a pretty good idea of what Dean got him, Castiel’s mouth still dropped when he opened the brown parcel. On top was his pink bra, but underneath were three different sets of bras and panties. Castiel blushed hard enough to feel heat in his cheeks. After closing the package, pacing around his room, reopening it, discovering a note with just Dean’s phone number on it, nearly having a heart attack, and then calling his old friend Meg, Castiel found himself entering Dean’s number into his cell with shaky fingers.

Dean heard his phone beep but was in the middle of a stack of papers, so he didn’t get to it right away. When he did it was his turn to drop his jaw. He figured it must have been fucking Christmas because Castiel had sent a full body selfie from the neck down. He was wearing the matching set of lacy, orange, see-through boyshorts and bra. The quality wasn’t great, but Dean zoomed in on the boy’s cock anyway. He was pretty sure Cas had a chubby.

Dean sat back and readjusted himself.  It felt as like all the blood in his body had just gone straight to his dick. He checked the time, Cas had sent the text twenty four minutes ago. He was probably freaking out.

 **Dean:** Goddamn, baby. Is it my birthday?

Castiel immediately texted back.

 **Cas:** thought you hated it

Dean had sent a second text at the same time.

 **Dean:** Sorry, was grading papers

 **Cas:** oh

 **Dean:** You look fucking amazing, Cas

 **Cas:** yeah?

 **Dean:** Fuck yeah, baby. Already got me getting hard

Dean barely hesitated before leaning back and snapping a shot of his bulge, framing a hand around it so the fabric would pull and Cas could get a good outline.

 **Cas:** fuck

 **Dean:** Like what you see, Castiel?

 **Cas:** absolutely, Mr. Winchester

 **Dean:** Cheeky ;)

Dean’s eyebrow had cocked in surprise. It seemed as though Cas could let himself be more forward through writing. Dean would enjoy exploring more of this later.

 **Dean:** Speaking of cheeks…J

Castiel felt his stomach flip. But deciding to go for broke, he got up, dropped his pajama bottoms and, making sure to cant his ass for the best possible angle, sent another mirror selfie to his teacher.

Up until very recently Cas hadn’t ever entertained the idea of wearing anything like this, but somehow it felt right. The pretty fabric squeezed against him in the most wonderful way, and he’d never thought of his breasts as sexy before, just… there. But with these on and Dean’s apparent appreciation he felt amazing, invincible, and decidedly sexy as fuck.

 **Dean:** Goddamn, baby. Always so busy with your tits I forget how hot that ass is

 **Dean:** Fuck, I love that little tail and those plump, little cheeks just hanging out, fucking perfect bubble butt. Bet you taste as good as you look, little cow

Cas had no idea how to respond. He huffed and pressed his lips together and decided to go for the truth.

 **Cas:** wish I could kiss you rn

Dean palmed himself and groaned. His cow really was fucking perfect.

 **Dean:** Me too baby. Would treat you so right

 **Dean:** Christ I fuckin want you

 **Cas:** want you too Dean

 **Dean:** Gonna touch yourself and think about me tonight, baby?

Castiel whimpered. He already was. His hand was down his panties, tugging slowly on his dick. Instead of typing back anything he sent another picture. In it Dean saw some of Cas’ tummy, with tiny little rolls near the waist band of the panties and his hand shoved down under. Dean could make out the pink tip of his cock pressing up against the orange lace and a smattering of dark curls providing a beautiful contrast against his skin tone and bright fabric. Dean complimented his own good taste.

 **Dean:** Fuck your prick is gorgeous

Dean’s immediate response was to want to call him so they could both hear each other jerk off, but he stopped himself. He realized more so that he wanted to stretch this out a bit longer.

 **Dean:** Now I want you to lie down, keep your bra and panties on, and keep jerking that cute little cock of yours. And when you’re about to come I want you to stick a finger up your ass just as far as it wants to go. Don’t push too hard. Get it nice and wet with your spit…  And after you’re done coming and screaming my name into the pillow, I want you to keep the panties on.  Wear them to school tomorrow.

Castiel wanted to do as instructed, but as soon as he read the last line he jerked his cock one more time and came. His hole still felt kinda funny and strangely needy, so in his post orgasm haze he laid down, took an index finger, and rubbed at his little hole. He gasped when the end of the finger easily slipped in past the ring. Cas held it there for a few moments before gently moving it in and out. He wasn’t sure if he liked it; it felt strange. But Dean had asked him to, and Castiel always did his homework.

 

 **Dean:** Don’t wear the hoodie today, baby ;)

Castiel had woken up to Dean’s text in the morning and felt a strange rush of excitement and embarrassment, but he did as instructed and felt a thrill run up and down his spine when Dean caught sight of him. It had triggered a flurry of texts praising Castiel for being such a good boy, for looking so amazing.

Castiel had smiled to himself and bit his lip. He didn’t have much in the way of provocative clothing, but Mr. Winchester seemed to appreciate whenever he wore tighter fitting t-shirts. Under his black t-shirt Cas could feel the bra and panties hugging him closely. The panties felt a little strange, the front stiff from last night’s come, but it wasn’t necessarily bad, and every time Cas moved and felt his cock press against the stain his stomach flipped, remembering that it was Dean who had made him come, and Dean who had wanted him to keep wearing the panties.

The chorus of praises from Dean continued, and Castiel had never felt so warm, which was in part how he had ended up agreeing to meet Dean during his lunch period in a janitor’s closet. Castiel didn’t know if he was more terrified or excited, he was so nervous at being caught but so turned on that Dean wanted him.

When he slipped in the room the light was already on and Dean was sitting near the back of the rather spacious closet, sitting on a stool with his hands on his knees.

“Hey, baby,” he said easily, slight smirk on his face.

Castiel swallowed and dropped his backpack, not quiet knowing what to say or do. He was pretty sure they were meeting here for sex. But what if it was something else, something different? What if Dean was breaking up with him? Could he even call it that at this point?

“Come here, little cow. Whatever you’re worrying about, just forget about it right now. I just wanted to see you, couldn’t wait any longer. Kept on sneaking looks at those pictures you sent last night.”

Castiel let go of the breath he didn’t realize he was holding and walked up to Dean. He didn’t say anything, just walked up to his knees and titled his head, looking down at Dean’s beautiful face. Dean licked his lips and Cas, unbeknowingly, followed suit. Dean smiled again and reached a hand up to rub an ear between two fingers.

“They’re a dead giveaway, you know?”

“What is?”

“Your ears. When you’re nervous or excited, they start twitching like crazy. And this,” he said, leaning forward and reaching around to give Cas’ tail an extremely gentle tug, “when you’re turned on? Gets stiff. Kinda reminiscent of something else, don’t ya think?” Dean finished with a smile, eyes lidded and purposefully looking Castiel up and down.

Castiel’s mouth went dry and he started rapidly swallowing.

“Shh, shh, shh, baby cow,” Dean said, finger pushed up against Castiel’s mouth. “It’s okay, baby. ‘M not gonna do anything you don’t want me to do.”

And as Dean said that he took his finger and pushed it past Castiel’s lips, resting it just lightly in his mouth, waiting to see what Cas would do.

Castiel, acting on instinct, wrapped his lips around Dean’s finger and gave it one quick suck. Seeing Dean smile, Castiel did it again, gently holding the tip of Dean’s finger between his teeth and sucking in again.

“Damn, Cas. I’m not gonna be able to control myself with you. Look at me, already hard and all you’ve done is taste my finger. Fuck, so fuckin’ perfect I don’t know what to do with you, Cas.”

Castiel blushed and kissed Dean’s finger.

Dean just hummed and ran his hands up and down his arms.

“I know you were a good boy for me last night, Cas. Gonna tell me how you completed your assignment?”

Castiel blushed, rewet his lips, and then started talking. “I uhm, well, I-I wanted to do your assignment, M-Dean. I really did. But I… kinda messed it up.”

“You mean you’re not wearing those panties and bra after all, Castiel?” Dean said in a stern voice. If Cas just had not wanted to wear come stained undies to school that was perfectly understandable, but if he had lied about it earlier that morning – that would be unexpected and unacceptable.

“N-No, Mr. Winchester-”

Dean rolled his eyes at the name.

“-Dean. I’m wearing them, I promise!” Castiel quickly pulled down the waist band of his jeans to reveal a sliver of orange lace. “I just- I came before I could put my finger up my…hole. But I did everything else! You can see yourself! It’s just that I was already so hard, and I felt so good in your present, and then I read your text and I- I came.” Castiel finished sheepishly, eyes lowering and tail swatting between his legs.

Dean couldn’t help his smile and gave Cas’ shoulders a reassuring squeeze.

“That’s okay, baby. The important part is that your jerked that cute cock in your new panties and brought them with you to school. That’s my present, Cas. Getting to see your come stained panties and knowing you’ve been wearing them all day at school, that you got hard and jerked it to me, only me.

It was only me, right, baby?”

Castiel nodded vigorously, eyes opened wide.

“Yes, Dean! Only you, I swear! You’re so, so hot, Mr. Winchester. I couldn’t imagine anybody else!”

Dean’s eyes crinkled, and he knelt in and gave Cas’ neck a quick kiss.

“You like calling me Mr. Winchester, little cow?”

Castiel stilled and looked Dean in the eyes.

“I’m not sure.”

Dean nodded, looking off to a side as one hand rested on Cas’ hip.

“I don’t like my partners to call me Mister or Master or whatever else. I like being in control, sure, but I also like being on equal footing. But I guess equal footing means letting you call me what you want, right, Cas?”

Dean looked up expectantly.

Castiel’s head tilted a bit before nodding slowly.

“Okay, so if you wanna keep on calling me Dean, go ahead, and if you wanna go back to calling me Mr. Winchester, well, I’m sure I could learn to deal for you.”

Castiel’s smile was big and genuine.

“Like calling you both, Dean.”

“That works too, Cas.”

They both stood still and kept looking at each other, Dean holding Castiel’s blue eyed gaze and a little surprised the calfboy wasn’t breaking it. He was also a little surprised when he realized they were both just standing there and smiling like two love struck idiots.

“Okay!” Dean said, intentionally breaking up the moment. “Time for you to turn in your homework,” he said with a wink.

Castiel rolled his eyes and started lifting up his shirt.

“On second thought…” Dean said, shooing Cas’ hands away and lifting the shirt up himself.

He sat back down and whistled. Castiel was beautiful. His lithe body looked perfect with his two little udders being secured in their orange fabric. His dusky nipples were already erect and straining against the lace, which made a lovely pattern over his skin.

Dean palmed both breasts and then moved his hands to the side, letting his thumbs pet Cas’ nubs.

“So pretty,” he whispered, wanting Castiel to always remember how much Dean appreciated his beautiful body.

His fingers then scaled down Cas’ tummy, igniting goosebumps in his wake, and then he rested the pads along the top of Cas’ jeans. Casually he gripped a hip in one hand and trailed fingers down Castiel’s slight bulge with the other.

He hummed and then murmured, “Gonna enjoy seeing my present, little cow. I loved getting milk from those titties. Now I’m gonna get some more cream from your prick. Such a good, little cow. Always taking care of his teacher, always making sure I have enough to drink.”

Dean gave Cas a squeeze and he gasped.

“Did you enjoy coming in your present, Cas? Did you say my name into a pillow like I asked?”

“N-no, Mr. Winchester. I mean yes, Mr. Winchester! I liked c-coming in your present. But I didn’t have time to say your name into a pillow. I came while sitting up.”

“You did?” Dean asked in a singsong voice. “What would you do a silly thing like that?”

“B-because I couldn’t lie down soon enough. I-I came too quickly, Dean. I’m sorry.”

“Aw,” Dean cooed. “That’s okay, little calf. Next time though I want you to do a better job at following instructions. I tell you to do things a certain way because I care, Cas. Because I have experience and I want what’s best for you. But I know you’re a good boy, and you’ll try harder not to come yourself too quickly next time, right, Castiel?”

“Yes, Mr. Winchster.”

“Good boy. Now, about that homework. I’m afraid that though I trust your word, I’m gonna have to see it for myself.”

Castiel nodded and quickly started undoing his pants.

“Slower, Cas. Wanna see everything.”

Castiel stopped and, with pants unbuttoned and zipper halfway down, slowly palmed his cock before running a hand up his stomach.

“I’m sorry, Mr. Winchester. I’m just so eager to show you I did a good job.”

“Fuck,” Dean whispered. “Take ‘em off. Now.”

Castiel smiled and quickly finished shoving off his pants. When he stood back up he made a point to keep his hands to the side despite wanting to cover his junk up.

“Shit, Cas,” Dean said before getting up off the stool and kneeling down in front of Cas. He could see where Cas had come himself. It made Dean’s dick ache.

Before the student knew what was happening Dean had licked a broad stripe up Castiel’s crotch. Cas involuntarily bucked his hips forward and Dean’s hands instantly went up steady his movements. Relentlessly he started licking at Castiel’s dick through his undies. Cas was hard and his dick was slanting up and to the right. Dean’s mouth moved off his dick and then started sucking the come stain from Cas’ panties. It was bitter and kind of funky and Dean loved it.

“Ah, Mr. Winchester!” Cas cried as Dean’s mouth moved to suck on Castiel’s sack through the panties.

Dean pulled off and smiled at Cas, “You like that, baby? Like having your teacher suck you off through your dirty, fucking panties?”

“Y-yes, Dean! Gonna - gonna come soon, Dean!”

“Oh, no, not yet, baby slut.”

Dean sucked a mark onto Castiel’s tummy and then pushed himself back up.

“Can’t have my best boy blowing his load yet. Haven’t even gotten to taste you, Cas.”

Castiel’s eyes went big again. He had almost forgotten Dean’s fascination with his tits.

Dean smiled and pulled Castiel to him, slowly and sweetly kissing the boy back into relaxation. Castiel was becoming pliant in his arms again, following Dean’s body’s movements and letting himself rut up against the man. Dean pulled back some and then ran his fingers over Cas’ boobs.

“Did you play around with the top, Cas?”

Castiel shook his head.

“Aw, now that’s a damn shame, baby. Cuz this set is a special set. Got a real nice surprise for you.”

Dean kissed Cas’ forehead and then brought him back in for another kiss, slowly backing the boy up against the wall. Cas moaned when his back hit the wall and Dean chuckled, knowing that Cas really was going to be a fucking handful in the sack as soon as he got over his culture’s repressive bullshit. The kid loved being manhandles and pleasing. It made Dean’s stomach swoop.

“Gonna take care of you, little cow. Gonna make you feel so good,” he murmured in between kisses.

Dean started kissing and licking on Cas’ neck, which Castiel immediately bore and didn’t stop himself form groaning at how good it felt.

“Did I do good, Mr. Winchester?”

“Hmm?” Dean asked, hazy from lust.

“On my homework. Was I good?”

“Shit, Cas,” Dean said before palming Cas’ tit and licking his collar bone. “You got a fuckin’ A, baby. Fuck, you looked so good, stiff cock pressing up against those pretty panties, fucking day old come stain on the front. Did you like it, Cas? Did you like feeling your perfect cock up against your own mess all day long? Did you like going to sleep with a wet stain on the front?”

Dean ground down into Castiel’s crotch, enticing the boy to moan again and grip the back of his shirt. Cas was hard, Dean wasn’t sure how much more the boy could take, but he was more than happy to find out.

“Y-Yes, Mr. Winchester! I liked it, I fucking loved it. I felt so fucking dirty all day long. Sitting in class with boring, old Adler going on about geometric shapes, everybody just sitting there looking stupid, but I’ve been half hard all day and nobody knew! I’ve been wearing fucking bra and panties that my teacher bought me and made me come in and told me to wear to school and nobody fucking knows, fuck!” Cas cried, losing control and humping Dean’s thigh.

“It feels so fucking good, Mr. Winchester. I fucking love feeling so dirty!”

“Fuck yeah, Cas, fuck yeah you do, baby cow. Fucking come here,” Dean said as he realigned their bodies together so he could rub his dick against Cas’.

“Such a dirty, fucking mouth when you’re turned on, Cas. Fuck, gonna train you up so good, baby. Gonna love using that dirty fucking mouth. _You’re_ gonna love using that dirty fucking mouth. Come for me, Cas. Come on, baby. Come your panties one more time.”

“Yes, yes, god, fuck, Mr. Winchester!” Cas cried as he continued thrashing against Dean, unable to stop himself from orgasming. His semen pushed through the lace and ended up getting on the front of Dean’s slacks but neither of them noticed.

Dean felt fat beads of pre-come push out of his dick as he watched Castiel hump himself into completion. His eyes screwed up tight and groaned out the most beautiful sounds Dean had heard in a long time. Dean licked into his mouth and felt his dick twitch in anticipation. As soon as the boy’s body had started calming down Dean began licking and sucking at his neck, moving closer and closer to his tits.

Castiel groaned, body feeling so sensitive, but didn’t stop Dean from kissing him.

“Fucking beautiful, Cas. You come so beautifully, angel. Gonna make you come over and over again, little cow.”

Dean kissed in between Cas’ small breasts and then licked up the breastbone, putting a lot of pressure into it. The air felt cool against the trails that Dean was leaving all over his skin. He felt his hole do that clench thing again, as if it were trying to latch on to something. He couldn’t stop himself from imagining it grabbing onto Dean’s dick. And that thought led to Castiel wondering what Dean tasted like; he could feel his mouth watering.

“Dean,” Castiel moaned. “Can’t wait to taste you, Dean. Please, Dean. Please let me suck you off. I – I’ve been reading a lot of guides and watching instructional videos. I think I can do it well, Mr. Winchester. Please let me try to suck you off, Dean. Please! I wanna taste you so bad, Mr. Winchester! You always taste me, but I never get you!”

“Shit, Cas. You been studying how to be a good, little cock slut for me? Christ, you’re such a perfect, fucking student, such a good little slut for me. So fucking smart. Gonna give you what you want. But I gotta show you one more thing first, little cow. You trust me, Cas?”

“Fuck yes, Dean.”

“Good,” he said with a quick kiss right above the lining to one of the cups. The bra didn’t give the illusion of Cas having bigger tits, Dean knew the boy was self conscious of his body still, but they really did give them a nice frame, and Dean fucking loved pretty lingerie. He had several more items he intended on giving the boy. But this one might possibly be his favorite.

“Did you know this is a maternity bra, Castiel?” He asked, leaning over the calfboy with one hand above Cas’ head and the other playing with a nipple.

Cas shook his head. “A maternity bra? What does that even mean?”

“It means, baby slut, that you can still wear it while nursing a baby. Or, in your case,” Dean continued, fingers playing with the strap where it met the cup, “while getting milked.”

Castiel’s mouth went dry. He had only been halfheartedly listening to Dean, still blissed out by his orgasm, but the last part got his attention. He still didn’t know how he felt about getting off and milking. On one hand it was absolutely _dirtybadwrong,_ but on the other, it felt _so_ good…

Dean seemed determined to help Castiel make up his mind, because before he could say anything else Dean undid the latch hidden at the top and suddenly Castiel’s right tit was completely popped out, framed by a triangle of orange material. The cup was still sewn on at the bottom and the material hung down almost obscenely. Castiel tensed, it wasn’t much different than before, the bra was extremely see-through, but somehow he felt much more exposed.

“Fuck,” Dean whispered. Unable to control himself he swiftly knelt down and started sucking on Cas’ tit.

Castiel cried out, startled. Dean usually worked his way up to milking, kneading Cas and talking to him, telling him he was doing good. This was unexpected, even for Dean.

“D-Dean!” he cried.

Dean lifted his head up. A fat bead of milk pearled at the end of Cas’ nipple. Dean swiped it up with a finger and then brought it up to Cas.

“Taste it, baby. Taste how good you are.”

“Dean, I – this is… I don’t know about this.”

“Okay, baby. I get it, I understand. It’s just that it tastes so sweet, you taste so sweet, and I think that if you tried it out you would understand. But I get it. Going against convention is scary. It ain’t for everyone, sweetheart.”

Castiel puffed out his chest which Dean loved.

“It’s not that I’m afraid of defying convention, _Mr. Winchester_ ,” Castiel snapped. “It’s just that I… well, I…”

“Well you what, Cas?”

“This is… I-“

“Cas, if you don’t want to try it then don’t. But if you do…” Dean stuck the finger in his mouth and softly moaned. “If you do, then don’t let that ugly voice in your head telling you that it’s dirty and wrong stop you. You’re not hurting anyone by doing it. You’re only hurting yourself by never knowing.”

Castiel couldn’t refute Dean that, so he nodded. Dean kissed him and then went back to kissing his chest and neck - minding not to touch Cas’ breasts with his mouth. If Castiel was going to be on the fence about this then Dean was going to tease him until the kid finally decided one way or the other.

Soon the boy was huffing and moaning and trying to push his chest and pelvis back up against Dean. That hadn’t taken long, Dean thought with a smirk.

His large hands had moved down to Castiel’s ass, giving his cheeks a good squeeze before trailing his fingers down and playing with the lining of his panties. He pressed them in against the cleft, loving how close he was go finally getting to what he wanted. Occasionally he would run his hand down Cas’ tail, and though he was now kissing between Cas’ tits he still was denying the boy his mouth on his udders. Not until the boy asked nicely.

“Dean!” Castiel all but yelled, exacerbated. “Please, Dean. Go back to sucking on my tits. I need them to get milked again, Dean.”

“Are they hurting you, Cas?”

“N-no, Dean.”

“Then they’re not that full. Now stop bossing me around and let me enjoy the rest of you.”

Castiel ran his hands down Dean’s back and cupped Dean’s ass. He always imagined savoring the first time he got to do that, but he was too distracted by the strong urge to have Dean milking him again.

“Please, Dean. I’m sorry! I didn’t mean to boss you around. I just, ugh,” he cried, trying to push his tit against Dean’s mouth. “I just want to feel you back on them again.”

Dean lifted his head up and tsked.

“Now is that how we ask our teachers for help, Castiel? By demanding and then trying to sneak one of these pesky, little udders into teacher’s mouth when you think he’s distracted?”

Castiel shook his head no, cheeks turning a nice shade of pink.

“Look at me when I’m talking to you, Castiel.”

Cas shuddered and lifted his head. His hands clasped in front of him, his bottom lip started trembling. He really did hate being in trouble, but Dean knew he needed to be firm this time.

“Now, Cas. There’s no need to get upset. You were naughty and now you need to make up for it. Get on your knees, baby boy. Use your pants for a cushion.”

Castiel did as instructed, sitting up straight with his legs folded under him. Dean reached down and fondled a velvety ear.

“Now I’m gonna stand here and pleasure myself. And you’re gonna keep your hands to yourself. I am going to come on you, but you are not going to get to taste it. IF you are good I will think about sucking the milk out of your tits, but one more mess up, and I’m afraid I won’t be milking you for a week. You’ll have to use a pump or figure out how to do it on your own, little cow. Are we clear?”

Castiel nodded, genuinely sad that he wasn’t going to be able to taste Dean’s cock.

“Awesome. Now sit on your hands, little calf. It’s for your own good, so you don’t impulsively reach up and grab my cock. This cock is only for good cows. Do you understand me?”

As Dean was talking he undid his slacks and let them fall to his feet. Castiel sat on his hands but still looked up at Dean, eyes big and plush lips shut. Dean bit down on his own bottom lip as he rubbed over his cock.

Castiel nodded that he understood Dean’s rule.

“That’s right baby.”

Dean lowered his boxer briefs; his dick slapped against his stomach.

“Now since you weren’t too bad I’m still gonna let you get marked up by my come, Castiel. But mark my words, if you keep up that bratty, demanding boy shit you won’t even get that. Now I know you’re a good boy, Cas, so don’t cry, but even good boys mess up and need to be taught a lesson now and again, right, Castiel? Nobody expects you to be perfect all the time. But I do expect you to own up to your mistakes.”

Dean gripped his cock and stepped out of his pants and walked closer to Cas. He spit on his hand and then brought it back down, gathering up the pre-come in his palm and then working it down his thick shaft.

Castiel’s eyes were huge. He had known Dean’s cock was big but seeing it this close was something else. He doubted he’d ever be able to get the whole thing in his mouth, let alone his ass. Still, he felt his fingers twitch beneath him. He desperately wanted to touch.

Dean’s cock looked almost angry it was so red, but the sounds Dean made while stroking himself were anything but. It was soothing, really, finally hearing what Mr. Winchester sounded like while jerking off. It was also beautiful.

Castiel licked his lips as he watched another fat bead of pre-come push out of his teacher’s dick. Dean smirked and brought his dick closer to Castiel, who instinctively sat up taller so his face was closer.

“Keep those hands behind your back, baby.”

Castiel complied and clasped his hands behind his back. He could feel his tail twitching wildly back and forth. He bit down on his lips as he watched the head of Dean’s cock jolt up and down in front of him.

“Keep that mouth closed, Cas,” and Dean took his dick and prodded at Castiel’s mouth. Cas did well though and kept his lips closed tightly, even though he was dying to open up and taste Dean. A long strand of pre-come followed Dean’s dick from Castiel’s pink lips as he pulled back slowly, watching it elongate until it broke. It swung down and hung off his chin, and Dean was certain Castiel wanted to rub it off or suck it in or do anything with it, but he was being such a good boy and kept his mouth shut.

“Very, good, Cas,” Dean said between grunts, starting to lose his control and thrust hard into his own hand. “I’m very impressed.”

Castiel whined at the praise and Dean took a step back, feeling his balls clench at the noise.

“Fuck, Cas” was all the warning he gave before he came. Fat globs of come came spurting from his dick. At first Dean got some on Cas’ chin and shoulder, but then his aim got better and he was able to get most of it all over Castiel’s tits.

Castiel moaned and arched his back into the hot ropes of come coming out of Dean’s cock. Dean was getting his seed all over Castiel’s chest and bra, and the boy would have only been happier if it had been in his mouth.

“Ah, fuck, Mr. Winchester, please, mark me! Get it all over me, please, Dean, please!”

“Cas!” Dean cried out as he milked the last bit of come out of his shaft. He stepped closer and wiped his softening dick all over Castiel’s face. The boy just moaned and chased after the tip, somehow remembering that he was supposed to keep his mouth closed. He just wanted to feel dean’s warm cock against his lips, even if he couldn’t taste.

“Fuck, so good, Cas. You’re so good. Come here, baby cow.”

Castiel’s hands had miraculously stayed clasped behind his back, but now they were in Dean’s hands. He was trembling as his teacher helped him up. Cas was so turned on he didn’t know what to do.

“Please, Dean, help me,” he mewed.

“Fuck,” Dean replied before kissing the boy for all he was worth. He kept Cas from pressing in, however. There was something he wanted to do first.

Dean placed Cas back up against the wall, making soothing sounds and touches as he did. Then he ducked down and took a long, broad swipe with his tongue, starting near Cas’ ribs and going up and over the cupped tit.

“Dean,” Castiel moaned.

“Gonna give you what you need now, babe.”

Dean kneaded Cas’ udder slowly, gently pushing out a weak stream of milk. It ran down Castiel’s tit, going around a glob of Dean’s semen.

Dean’s tongue immediately darted out and licked it up, combining his bitter come with Castiel’s sweet milk. He moaned his appreciation loudly. It was one of the best things he’d ever tasted.

“Fuck, Cas. Knew we’d taste so good together, baby. Christ, busting my nut all over you, taking it like such a good, grown up Cow. Letting me taste it with your sweet milk. Fuck, I fucking love this, Cas.”

Castiel whined and pushed his chest back out. Dean got the hint and shut up and started tonguing Castiel’s nipple, making sure to swirl his tongue through his own seed and then sucking out more milk.

Castiel was hard again, and it was taking all of his patience to keep his hands out of his panties.

“Please, Dean, Please. Please can I taste?”

Castiel was almost surprised at his own request. He thought he was gonna ask Dean for permission to come again, but instead that had come out.

“Fuck, Cas. You mean it?”

Castiel nodded his head.

“Come on, Cas. You know the rules by now. Gotta hear you say it, babe.”

“C-Can I please taste us, Dean? Your come and my milk?”

Dean shut his eyes and breathed through his nose. He instantly wanted to turn Cas around and fuck him. Hard. But that wasn’t an option right now.

Silently Dean took a swab of his come and brought it to Cas’ lips. Castiel opened his mouth and stuck out his tongue. Dean dabbed the semen onto the boy’s waiting tongue and Castiel quickly closed his mouth, sucking it down.

Dean smirked and kissed Cas’ nose as the boy groaned. Dean tasted kinda bitter, kinda strange… different then his own semen. But it was perfect. Dean was perfect.

“Ah, little cow, I didn’t say swallow.”

Castiel’s eyes popped open but before he could start apologizing Dean smiled and kissed his lips.

“That’s okay, you’re still in training. Plus, you earned it, baby boy. Did so good not opening your mouth. I know how bad you wanted it, baby. I’m so proud of you.”

Castiel blushed, but his smile was still beaming.

“I’ll never get tired of those red cheeks, sweetheart. Now, open your mouth again, but this time no swallowing. Okay?”

“Yes, Dean.”

Dean swiped another glob of come, this time off Castiel’s chin, and placed it on the boy’s tongue for a second time. Then he quickly leaned down and suckled Castiel’s udder, getting a mouth full of sweet, warm milk but not swallowing either. He leaned in and kissed Cas, sealing their lips together and letting Cas’ milk drain back into his body. Castiel’s tongue darted into Dean’s, helping the liquid move into his own mouth.

He rubbed his tongue against the roof of his mouth, trying to mix the two together and being in absolute heaven. It was perfect. His milk balanced out Dean’s come. Cas was sad when he swallowed it down; he wanted more. However, Dean was already pressing their bodies together, realigning their mouths and giving him a deep kiss. Cas felt his heart swell. And then he felt his chest press up against Dean’s, getting Dean’s come all over his own shirt. Castiel wondered if he had another, but immediately forgot when he felt Dean’s hand palm his ass. He whimpered when Dean broke the kiss.

“Can you come over after school?” Dean panted in his ear.

**Notes for the Chapter:**

> Every time I post I wait for everybody to stop subscribing and reading and then kick me out of town.


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